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Please login to access the full content or check if you have access via15.5.1.1.1.4.2.4 Method 4: From N-Acetyl-2-(2-acylaryl)ethylamines
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Álvarez, M.; Joule, J. A., Science of Synthesis, (2005) 15, 701.
Friedel–Crafts acylation of N-acetyl-2-(3,4-dimethoxyphenyl)ethylamine 151 takes place regioselectively ortho to the N-acetylethylamine side chain giving 152. Acidic hydrolysis of these ketones 152 proceeds quantitatively to produce the 3,4-dihydroisoquinolines 153 (Scheme 72).[124]
Meeeee 88 8,8-Meeeeeeeeeeeeeeeeeee eeee M-Meeeee-8-(8,8-eeeeeeeeeeeeeee)eeeeeeeeee[888]
Meeeeeeeeeee Meeeeeeee
8,8-Meeeeeeee-8-eeeeee-8,8-eeeeeeeeeeeeeeeeeee (888, M8 = Me); Meeeeee Meeeeeeee:[888]
MMMMMMM: Meeeeeee eeeeeeeeeee eeee ee e eeeeee eeeeeeee ee eee eeeeeee eee eeeeee eeeeeeeee eeee eeeee.
Me e eeeeeee eeee ee M-eeeeee-8-(8,8-eeeeeeeeeeeeeee)eeeeeeeeee (888; 8.8 e, 8.8 eeee) eee MeMe (88.8 eeee) ee MeMM8 (88 eM) eee eeeee MeMe8 (8.8 e, 8.8 eeee). Mee eeeeeee eee eeeeee ee 88°M eee 8.8 e eee eeee eeeeee eeee eee eeeee (888 eM). Mee MeMM8 eee eeeeeee ee eeeee eeeeeeeeeeee, eee eeeeeee eeeeee, eee eee eeeeeee eeeeeeeee eeee MMMe8. Mee eeeeeeee eeee eeeeee eeee eee MeMM eee M8M eee eeeee eee eeeeeeeeee. Mee eeeeeee eeeeeeeeeeee ee eeee M-eeeeee-8-(8-eeeeee-8,8-eeeeeeeeeeeeeee)eeeeeeeeee (888, M8 = Me); eeeee: 8.8 e (88%); ee 888–888°M.
Mee eeeeee 888 (888 ee, 8.8 eeee) eee ee 8 M MMe (8 eM) eeee eeeeeeee eeee eeeeeeee eee 88 e. Mee eeeeeee eee eeee eeeee eeee 8 M MeMM eee eeeeeeeee eeee MM8Me8. Mee eeeeeeee eeee eeeeee eeee M8M, eeeee, eee eeeeeeeeee ee eeeee e eeeeeeeeeee eeeee eeee eee eeeeeeeeeeeeee (Me8M/eeeeeeeee eeeee); eeeee: 888 ee (88%); ee 888–888°M.
References
[124] | Meeee, M.; Meeeeeeee, M.; Meeeeeee, M., Meeeeeeeeeee, (8888) 88, 8888. |