Acetic Acid → 5-[4-(5-Fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentylidenamino] quinoline-2-carboxylic acid methyl ester

HRID 2054984Notes

Reaction equation

HRID 2054984 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[NH2:15])[N:6]=1)=[O:4].[F:16][C:17]1[CH:18]=[CH:19][C:20]([O:35][CH3:36])=[C:21]([C:23]([CH3:34])([CH3:33])[CH2:24][C:25]([OH:32])([C:28]([F:31])([F:30])[F:29])[CH:26]=O)[CH:22]=1.C(O)(=O)C.CCCCCC.C(OCC)(=O)C>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[N:15]=[CH:26][C:25]([OH:32])([C:28]([F:29])([F:31])[F:30])[CH2:24][C:23]([C:21]2[CH:22]=[C:17]([F:16])[CH:18]=[CH:19][C:20]=2[O:35][CH3:36])([CH3:33])[CH3:34])[N:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 115731224-(5-Fluoro-2-methoxy-phenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanalHCID 21226206Ethyl acetate hexaneHCID 45089604Methyl 5-aminoquinoline-2-carboxylate

Product 1

HCID 692058395-[4-(5-Fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentylidenamino] quinoline-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Analogously to Example 37, 200 mg (1.0 mmol) of 5-aminoquinoline-2-carboxylic acid methyl ester is reacted with 371 mg (1.2 mmol) of 4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanal and 1.10 ml of concentrated acetic acid in 20 ml of toluene. After chromatography on silica gel with hexane-ethyl acetate (0-100%), 420 mg (85% of theory) of the product is obtained.

Sources & evidence

ORD record
ord-15e04037162c4b30b31039701af777fe
Source dataset
uspto-grants-2008_02
Patent number
US07329753B2

Reaction notes

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