Chloroacetyl chloride → HCID 12369645, compound

Participants

Reaction Steps

1-(2-[2-chloro-acetyl]amino-3,4-dimethoxybenzyl)isoquinoline was prepared from 5.9g (0.02 mol) of 1-(2-amino-3,4-dimethoxybenzyl) isoquinoline dissolved in 400 ml. of ethyl acetate, and stirred for 2 hours with 15 ml. of chloro-acetyl chloride. The precipitate which formed was filtered and dried to yield 7.1g (87%) of the hydrochloride salt, mp 193°-194°, which was suspended in 200 ml. of water and stirred for 10 min. with 10% Na2CO3 solution. The free base was extracted with chloroform, and the organic layer was washed with water, dried (sodium sulfate) and concentrated to yield a residue which was crystallized from methanol to give the pure base; mp 166°-167°; maxKBR 1650 cm-1 (aminde C=0); δtmsCDCl3 3.75 (s, 3, OCH3), 3.90 (s, 3, OCH3), 4.20 (s, 2, CH2Cl), 4.55 (s, 2, CH2), 6.63-7.00 (m, 2, aromatic), 7.23-7.85 (m, 4, aromatic), 8.20-8.45 (m, 2 aromatic) and 9.80 (broad s, 1, NH).

Provenance & Evidence