4-Chlorobenzylamine → HCID 178482192, compound

HRID 2119331Notes

Reaction equation

[OH:1][C:2]1[C:11]2[C:6](=[C:7]([NH:19][CH3:20])[CH:8]=[C:9]([CH2:12][N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:21](OCC)=[O:22].[Cl:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31][NH2:32])=[CH:29][CH:28]=1>>[Cl:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31][NH:32][C:21]([C:3]2[CH:4]=[N:5][C:6]3[C:11]([C:2]=2[OH:1])=[CH:10][C:9]([CH2:12][N:13]2[CH2:14][CH2:15][O:16][CH2:17][CH2:18]2)=[CH:8][C:7]=3[NH:19][CH3:20])=[O:22])=[CH:29][CH:28]=1

Participants

Reactant 2

HCID 660364-Chlorobenzylamine

HCID 178469660HCID 178469660, compound

Product 1

HCID 178482192HCID 178482192, compound

Conditions

Temperature: 200 °C

Procedure

A mixture of ethyl 4-hydroxy-8-(methylamino)-6-(4-morpholinylmethyl)-3-quinolinecarboxylate (280 mg) and 4-chlorobenzylamine (1.5 mL) is heated under nitrogen at 200° C. for 30 min. The bulk of the 4-chlorobenzylamine is removed under reduced pressure, and the product is purified by chromatography on silica gel to give 169 mg of the title compound as an oil.

Workup

customThe bulk of the 4-chlorobenzylamine is removed under reduced pressure
customthe product is purified by chromatography on silica gel

Sources & evidence

ORD record: ord-94219c6fef394932af79b857a1e922d1
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06686356B2

Reaction notes

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