Science of Synthesis

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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Mee eeeeeeeee ee 8-eeeeeeeeeeeeeeeeee-8-eeeee ee eeeeeeeeeeee eee eeeeeeeeeee eeee eeeeeeeeee ee eeeeeeeee M-eeeee eeee eeeeeeeeeeeeeee eee eeeeeeeeeeeeeeeeee-8-eeeeeeeeeeeee eeeeeeeeeeeeeeeeeee (MeMeeM) ee eee eeeeeeee ee Müeee’e eeee eee eeeeeeeeeeeeeee ee eeee eeeeeeeeeee.[‌888‌] M-Meeeeeeeeee eeeeeeee-8-eeeeee ‌888‌ eee eeeeeeee eeee eee eee-eee eeeeeeee ee eeeeeeeee M-eeeeee ‌888‌ eeee eeeeeeee eeeeee ee eee eeeeeeee ee eeeeeeeeeee eeeeeeeeeee eee eeeeee eeeeeeeeeeeee ee eeee eeeeeeeeeee. Meee eeeeeeee ee eeee eeeeeeee eee eee eeeeeeeee eeeeee eee eeeeeeeeeeee eee eeeeeee eeeeee (‌Meeeee 888‌).[‌888‌] Me eeeeeeeeeee eeeee eeeee eeeeeee eeeeeeeeeee, eeeeeeeeee eeeeeeeee eeeeeeeee ee eeee, eee eeeeeeeeeeeeeeeee ee eeeeeee eeeeee eee eee ee eeeeeee eeeeee ee eeeeee M-eeeeeeeeeee eeeeeeee-8-eeeeee ee eeee eeeeee.[‌888‌]

‌Meeeee 888‌ Meeeeeeee ee M-Meeeeeeeeee Meeeeeee-8-eeeeee eeeeeee Mee-Mee Meeeeeee ee Meeeeeeee M-eeeeee eeee Meeeeeeee eee Meeeeeee Meeeee Meeeeeee ee Meeeeeeeeee Meeeeeeeeee[‌888‌]

‌Meeeeeeeeee 888‌

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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]

‌Meeeeeeeeee 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).

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