Acetic Acid → 5-[4-(5-Fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentylidenamino]quinoline-2-carboxylic acid amide

HRID 2054955Notes

Reaction equation

HRID 2054955 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([C:12]([NH2:14])=[O:13])=[N:7]2.[F:15][C:16]1[CH:17]=[CH:18][C:19]([O:34][CH3:35])=[C:20]([C:22]([CH3:33])([CH3:32])[CH2:23][C:24]([OH:31])([C:27]([F:30])([F:29])[F:28])[CH:25]=O)[CH:21]=1.C(O)(=O)C.O>C1(C)C=CC=CC=1>[F:15][C:16]1[CH:17]=[CH:18][C:19]([O:34][CH3:35])=[C:20]([C:22]([CH3:32])([CH3:33])[CH2:23][C:24]([OH:31])([C:27]([F:30])([F:29])[F:28])[CH:25]=[N:1][C:2]2[CH:11]=[CH:10][CH:9]=[C:8]3[C:3]=2[CH:4]=[CH:5][C:6]([C:12]([NH2:14])=[O:13])=[N:7]3)[CH:21]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 115731224-(5-Fluoro-2-methoxy-phenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanalHCID 692036145-Aminoquinoline-2-carboxylic acid amide

Product 1

HCID 692028825-[4-(5-Fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentylidenamino]quinoline-2-carboxylic acid amide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution that consists of 290 mg (1.55 mmol) of 5-aminoquinoline-2-carboxylic acid amide, 616 mg (2.0 mmol) of 4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethyl-pentanal and 3.80 ml of concentrated acetic acid in 30 ml of toluene is refluxed for 20 hours in a water separator. Then, the solvent is removed in a vacuum. After the residue is purified on silica gel with hexane/ethyl acetate (0-70%), 438 mg (59% of theory) of the product is obtained.

Workup

  1. customThen, the solvent is removed in a vacuum
  2. customAfter the residue is purified on silica gel with hexane/ethyl acetate (0-70%), 438 mg (59% of theory) of the product
  3. customis obtained

Sources & evidence

ORD record
ord-9df40bd582714b5e9770e927b34cbbe7
Source dataset
uspto-grants-2008_02
Patent number
US07329753B2

Reaction notes

Loading…