4-(4-Chloro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanal → 5-[4-(4-Chloro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentylidenamino]-quinoline-2-carboxylic acid amide

HRID 2055008Notes

Reaction equation

HRID 2055008 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.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([CH3:33])([CH3:32])[CH2:23][C:24]([OH:31])([C:27]([F:30])([F:29])[F:28])[CH:25]=O)=[C:18]([O:34][CH3:35])[CH:17]=1>C(O)(=O)C.C1(C)C=CC=CC=1>[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([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)=[C:18]([O:34][CH3:35])[CH:17]=1

Participants

5

Reactant 2

HCID 219489374-(4-Chloro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanalHCID 692036145-Aminoquinoline-2-carboxylic acid amide

Product 1

HCID 692037995-[4-(4-Chloro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentylidenamino]-quinoline-2-carboxylic acid amide

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1140TolueneSolvent

Procedure

Analogously to Example 37, 160 mg (0.87 mmol) of 5-aminoquinoline-2-carboxylic acid amide is reacted with 341 mg (1.05 mmol) of 4-(4-chloro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanal in 0.96 ml of concentrated acetic acid and 20 ml of toluene. After purification on silica gel with hexane-ethyl acetate (0-100%), 340 mg (79% of theory) of the product is obtained.

Workup

  1. customAfter purification on silica gel with hexane-ethyl acetate (0-100%), 340 mg (79% of theory) of the product
  2. customis obtained

Sources & evidence

ORD record
ord-67514081a1ea4915b6018545c39cfdf0
Source dataset
uspto-grants-2008_02
Patent number
US07329753B2

Reaction notes

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