4-Chlorobenzylamine → HCID 178423370, compound

HRID 2289911Notes

Reaction equation

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

Participants

Conditions

Temperature: 210 °C

Procedure

A mixture of 230 mg of ethyl 4-hydroxy-6-methyl-3-quinolinecarboxylate (J. Chem. Soc., 893 (1948)) and 0.7 mL of 4-chlorobenzylamine is stirred for 1 h at 210 ° C. The mixture is cooled to 25° C. and it is diluted with 1.5 mL of toluene. The mixture is filtered and the filtrant is dissolved in a minimum volume of refluxing glacial acetic acid. The hot solution is treated with distilled water dropwise until it becomes cloudy, and it is allowed to cool to 25° C. The precipitate is collected by filtration and it is washed with a small amount of dilute aqueous acetic acid. The solid is dried for 48 h at 20 torr and 85° C. This procedure gives the title compound as 47 mg of a light tan solid.

Workup

temperatureThe mixture is cooled to 25° C.
filtrationThe mixture is filtered
dissolutionthe filtrant is dissolved in a minimum volume of refluxing glacial acetic acid
additionThe hot solution is treated with distilled water dropwise until it
temperatureto cool to 25° C
filtrationThe precipitate is collected by filtration and it
washis washed with a small amount of dilute aqueous acetic acid
customThe solid is dried for 48 h at 20 torr and 85° C

Sources & evidence

ORD record: ord-4cbbb293df144bc0b5d43f75eacf0b9b
Source dataset: uspto-grants-2000_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06093732

Reaction notes

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