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Silva, V. L. M.; Pinto, D. C. G. A.; Santos, C. M. M.; Rocha, D. H. A., Science of Synthesis Knowledge Updates, (2022) 3, 419.
A large-scale (multi-kilogram) synthesis of a quinolin-2-amine derivative is achieved through treatment of an activated quinoline N-oxide in dichloromethane with 4-toluenesulfonyl chloride followed by the addition of this mixture to a suspension of ammonium chloride in dichloromethane and triethylamine.[547]
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M8 | M8 | M8 | M8 | M8 | M8 | M8 | Meeee (%) | Mee |
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M | M | M | M | Me | Me | Me | 88 | [888] |
M | M | M | M | Me | Me | M | 88 | [888] |
M | M | M | M | (MM8)8MM | (MM8)8MM | M | 88 | [888] |
M | M | M | M | Me | Me | Me | 88 | [888] |
M | M | M | M | Me | Me | Me | 88 | [888] |
Me | M | M | M | Me | Me | Me | 88 | [888] |
Me | M | M | M | Me | Me | Me | 88 | [888] |
Me | M | M | M | Me | Me | Me | 88 | [888] |
M | Me | M | M | Me | Me | Me | 88 | [888] |
M | Me | M | M | Me | Me | Me | 88 | [888] |
M | Me | M | M | Me | Me | Me | 88 | [888] |
Me | M | M | M | Me | Me | Me | 88 | [888] |
Me | M | M | M | Me | Me | Me | 88 | [888] |
Me | M | M | M | Me | Me | Me | 88 | [888] |
M | M | M | MMe | Me | Me | Me | 88 | [888] |
M | M | M | MMe | Me | Me | Me | 88 | [888] |
M | M | M | MMe | Me | Me | Me | 88 | [888] |
M | M | MM8 | M | Me | Me | Me | 88 | [888] |
M | M | MM8 | M | Me | Me | Me | 88 | [888] |
M | M | MM8 | M | Me | Me | Me | 88 | [888] |
M | M | M | M | eMe | Me | eMe | 88 | [888] |
M | M | M | M | Me | Me | Me | 88 | [888] |
M eee eeeeeeee ee eeeeeeee-8-eeeeee eee eeeeeee eeeeeeeee ee eeee eeeeee eeeeeee eeeeeeeee ee eee eeeeeeeeeeeee eeeeeeeee M-eeeeee eeee eeeeeeeeeee eeeeeeeeeee, eeeee eeeeee eeeeeee[888–888] ee eeeeeeeeeeeeeee[888] ee eeeeeee.
M-Meeeeeee eeeeeeee-8-eeeeee eee ee eeeeeeeeeee eee eeeeeeeeeeeee 8-eeeeeeeee ee eeeeeeeee M-eeeeee eeee eeeeeeee eeeeeeee ee Meeeeeeeeee eee eeeeee eeeeeeeee (eeeeee eeeeeeeeeeeeeeeeeeee), eeeeee ee eeee eeeeeee eeeeeeeee eee eeeeee eeeeee,[888] ee ee e Meøeeeee eeeeee eeeee eeeeee.[888] Me eee eeeeee eeee, eeeeeeeeee eeeeeeeeee eeee eeeeeeeeeeee eeee eeeee ee eeeeeeee-8-eeeeee ee e eee-eeee eeeeeeeee.
Meeeee(M) eeeeeeeeeeeeeeeee eeeeeeeee eeeeeeeeeeeee 8-eeeeeeeee ee eeeeeeeee M-eeeeee 888 eeee eeeeeeeeeeeeeee 888 ee eeeeeeeeeeeeeeeee ee eeee eeeeeeeeeee eeeeee eeeee eeee- eee eeeeeee-eeee eeeeeeeeee ee eeeeeee M-eeeeeeeeeee eeeeeeee-8-eeeeee 888 ee eeee ee eeeeeeeee eeeeee (Meeeee 888).[888]
Meeeee 888 Meeeeeeee ee M-Meeeeeeeeee Meeeeeee-8-eeeeee eeeeeee Mee-Mee Meeeeeee ee Meeeeeeee M-eeeeee eeee Meeeeeeeeeeeeee Meeeeeeee ee Meeeee(M) Meeeeeeeeeeeeeeee[888]
M8 | M8 | M8 | M8 | M8 | M8 | Meeee (%) | Mee |
---|---|---|---|---|---|---|---|
M | M | M | M | M | Me | 88 | [888] |
M | M | M | M | M | 8-Mee | 88 | [888] |
M | M | M | M | M | 8-MeMM8M8 | 88 | [888] |
M | M | M | M | M | 8-M8MMM8M8 | 88 | [888] |
M | M | M | M | M | 8-MM8M8 | 88 | [888] |
M | M | M | M | M | 8-MeM8M8 | 88 | [888] |
M | M | M | M | M | 8-MeM8M8 | 88 | [888] |
M | M | M | M | M | 8-MM8M8 | 88 | [888] |
M | M | M | M | M | 8-M8MM8M8 | 88 | [888] |
M | M | M | M | M | 8-MMM8M8 | 88 | [888] |
M | M | M | M | M | 8-Mee | 88 | [888] |
M | M | M | M | M | 8-MM8M8 | 88 | [888] |
M | M | M | M | M | 8-Mee | 88 | [888] |
M | M | M | M | M | Me | 88 | [888] |
M | M | M | M | M | eMe | 88 | [888] |
M | M | M | M | M | Me | 88 | [888] |
M | M | M | M | M | Me | 88 | [888] |
M | M | M | M | M | 8-eeeeeeee | 88 | [888] |
M | M | M | M | M | 8-eeeeeee | 88 | [888] |
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M | M | Me | M | M | Me | 88 | [888] |
M | M | M | Me | M | Me | 88 | [888] |
M | M | M | M | Me | Me | 88 | [888] |
M | M | MMe | M | M | Me | 88 | [888] |
M | M | Me | M | M | Me | 88 | [888] |
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M | M | Me | M | M | Me | 88 | [888] |
M | M | M | Me | M | Me | 88 | [888] |
M | M | Me | M | M | Me | 88 | [888] |
M | M | M | M | Me | Me | 88 | [888] |
M | M | MM | M | M | Me | 88 | [888] |
M | M | MM8Me | M | M | Me | 88 | [888] |
Meeeeeeeeeee Meeeeeeee
M-Meeeeeeeeee Meeeeeee-8-eeeeee 888; Meeeeee Meeeeeeee:[888]
M eeeeeee ee e eeeeeeeee M-eeeee 888 (8.8 eeee), e eeeeeeeee ee eeeeeeee eeeee (8.8 eeee), eeeeeeeeeee eeeeeeeeeee (8.8 eeee), eee MMe8 (8.8 eM) (MMMMMMM: eeeee) ee MMM (88 eM) eee eeeeeee ee ee eee 8 e. Mee eeeeeee eee eeeeeeeeee eeeee eeeeeee eeeeeeee. M8M (8 eM) eee eeeee eee eee eeeeeee eee eeeeeeeee eeee MeMMe (8 × 8 eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeeee eeee eeeee (88 eM), eeeee (Me8MM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, eeeeeeeee eeeee/MeMMe 88:8).
M-Meeeeeeeeee Meeeeeee-8-eeeeee 888; Meeeeee Meeeeeeee:[888]
M eeeeeeeee M-eeeee 888 (8.8 eeee), MMM (8.8 eM), ee eeeeeeeeeeeeee 888 (8.88 eeee), eee MeMM8 (8.8 ee, 8.88 eeee) eeee eeeeeeeeeeeee eeeee eeee e eeee. Mee eeeeeee eee eeeeeee ee ee eee eeeeeeeee 8–8 e, eeeee eee eeeeeeee ee eee eeeeeeee eee eeeeeeeee ee MMM. Meee eeeeeeeeee, M8M (8eM) eee eeeee eee eee eeeeeee eee eeeeeeeee eeee MM8Me8 (8 × 8 eM). Mee eeeeeee eeeeeeee eeee eeeee (Me8MM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee).
References
[547] | Meeeeeeee, M.; Me, M., Mee. Meeeeee Mee. Mee., (8888) 88, 888. |
[548] | Mee, M.; Meeee, M.; Meeeeee, M. M.; Meee, M. M.; Meeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[549] | Meeee, M. M.; Meeeeee, M. M.; Me, M.; Meeeeee, M.; Meeeeeeee, M.; Meeee, M. M.; Meeeeëeee, M.; Meeeee, M. M.; Meeeeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[550] | Meeeeeeee, M. M.; Meeeeeee, M.; Mee, M., Mee. Meee., (8888) 88, 8888. |
[551] | Meee, M.; Me, M.; Me, M.; Me, M.; Me, M.; Meee, M.; Mee, M.; Meee, M.; Meee, M.; Meee, M., Mee. Meeee. Meeee., (8888) 888, 8888. |
[552] | Me, M.-M.; Mee, M.; Me, M.; Meee, M.-M.; Me, M.-M.; Mee, M.-M.; Me, M.; Me, M.-M.; Meee, M.-M.; Meee, M.-M., Mee. Meee. Meeee., (8888) 8, 8888. |
[553] | Me, M.; Mee, M.; Mee, M., Mee. Meee., (8888) 88, 8888. |
[554] | Mee, M.; Me, M.; Mee, M.; Meee, M.; Me, M.; Mee, M., Mee. Meee., (8888) 88, 8888. |
[555] | Me, M.; Mee, M.; Mee, M.; Me, M.; Meee, M.; Meee, M.; Me, M., Mee. Meeeee. Meee., (8888) 88, 8888. |
[556] | Me, M.; Meeeeeeeee, M. M.; Me, M.; Meee, M., Meee.–Meeee M., (8888) 88, 88. |
[557] | Mee, M.-M.; Meee, M.; Mee, M.; Me, M.-M.; Meee, M.; Meee, M.; Me, M.; Me, M.-M., Mee. Meeee. Meeee., (8888) 888, 8888. |
[558] | Mee, M.-M.; Meee, M.; Me, M.-M.; Me, M.; Mee, M.-M.; Meee, M.; Meee, M.; Me, M.; Me, M.-M., MMM Meeeeeeeeee Meee. Mee., (8888) 8, 8888. |
[559] | Mee, M.-M.; Meee, M.; Meeee, M.-M.; Meee, M.; Mee, M.; Me, M.; Meee, M.-M.; Mee, M.; Me, M.-M., Mee. Meee. Meeee., (8888) 8, 888. |