Water → 5-[4-(5-Fluoro-2,3-dihydrobenzofuran-7-yl)-2-hydroxy-4-methyl-2-trifluoromethyl-pentylidenamino]-2-methylquinoline

HRID 2220240Notes

Reaction equation

HRID 2220240 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:11]([CH3:22])([CH3:21])[CH2:12][C:13]([OH:20])([C:16]([F:19])([F:18])[F:17])[CH:14]=O)[C:5]2[O:9][CH2:8][CH2:7][C:6]=2[CH:10]=1.[NH2:23][C:24]1[CH:33]=[CH:32][CH:31]=[C:30]2[C:25]=1[CH:26]=[CH:27][C:28]([CH3:34])=[N:29]2.O>C(O)(=O)C.C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([C:11]([CH3:21])([CH3:22])[CH2:12][C:13]([OH:20])([C:16]([F:19])([F:17])[F:18])[CH:14]=[N:23][C:24]2[CH:33]=[CH:32][CH:31]=[C:30]3[C:25]=2[CH:26]=[CH:27][C:28]([CH3:34])=[N:29]3)[C:5]2[O:9][CH2:8][CH2:7][C:6]=2[CH:10]=1

Participants

6

Reactant 3

HCID 962WaterHCID 1486835-Quinolinamine, 2-methyl-HCID 441849894-(2,3-Dihydro-5-fluoro-7-benzofuranyl)-2-hydroxy-4-methyl-2-trifluoromethyl-pentanal

Product 1

HCID 441850445-[4-(5-Fluoro-2,3-dihydrobenzofuran-7-yl)-2-hydroxy-4-methyl-2-trifluoromethyl-pentylidenamino]-2-methylquinoline

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1140TolueneSolvent

Procedure

A mixture that consists of 4-(5-fluoro-2,3-dihydrobenzofuran-7-yl)-2-hydroxy-4-methyl-2-trifluoromethyl-pentanal (320 mg, 1 mmol) and 5-amino-2-methylquinoline (190 mg, 1.2 mmol) in acetic acid (2 ml) is stirred for 16 hours at room temperature, diluted with 10 ml of toluene and heated for 4 hours in a water separator. The batch is concentrated by evaporation, whereby the acetic acid is removed azeotropically with toluene. The residue is purified by column chromatography on silica gel with hexane-ethyl acetate: 274 mg of the product accumulates as colorless crystals.

Workup

  1. concentrationThe batch is concentrated by evaporation, whereby the acetic acid
  2. customis removed azeotropically with toluene
  3. customThe residue is purified by column chromatography on silica gel with hexane-ethyl acetate

Sources & evidence

ORD record
ord-f58beac18f8d4ae2bd5fb783049b46bb
Source dataset
uspto-grants-2008_08
Patent number
US07417056B2

Reaction notes

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