4-Chlorobenzylamine → HCID 178486814, compound

HRID 2289945Notes

Reaction equation

C(O[C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][C:12]([O:17][CH3:18])=[C:11]([O:19][CH3:20])[CH:10]=2)=[O:5])C.[Cl:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26][NH2:27])=[CH:24][CH:23]=1>C1(C)C=CC=CC=1>[Cl:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26][NH:27][C:4]([C:6]2[CH:7]=[N:8][C:9]3[C:14]([C:15]=2[OH:16])=[CH:13][C:12]([O:17][CH3:18])=[C:11]([O:19][CH3:20])[CH:10]=3)=[O:5])=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 190 °C

Procedure

A mixture of 6,7-dimethoxy-4-hydroxy-3-quinoline carboxylate ethyl ester (J. Am. Chem. Soc., 68, 1264 (1946)) (139 mg) and 4-chlorobenzylamine (0.61 mL) are heated at 190° C. for 1 h. The resulting mixture is diluted with toluene (1.5 mL) and allowed to cool to rt. The crude product is purified by column chromatography (dichloromethane/methanol; 100/1, 100/5) and recrystallization (acetic acid, water) to afford 26 mg of the title compound as a white solid.

Workup

temperatureto cool to rt
customThe crude product is purified by column chromatography (dichloromethane/methanol; 100/1, 100/5) and recrystallization (acetic acid, water)

Sources & evidence

ORD record: ord-285fdfc98183455980c2ac361bb320d5
Source dataset: uspto-grants-2000_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06093732

Reaction notes

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