4-Chlorobenzaldehyde → 5-(4-Chloro-phenyl)-1-(3,4-difluoro-phenyl)-3-hydroxy-4-isobutyryl-1,5-dihydro-pyrrol-2-one

HRID 869051Notes

Reaction equation

HRID 869051 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[F:9])[NH2:5].[Cl:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=1.C([O:21][C:22](=O)[C:23](=[O:30])[CH2:24][C:25](=[O:29])[CH:26]([CH3:28])[CH3:27])C>C(#N)C>[Cl:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]2[N:5]([C:4]3[CH:6]=[CH:7][C:8]([F:9])=[C:2]([F:1])[CH:3]=3)[C:22](=[O:21])[C:23]([OH:30])=[C:24]2[C:25](=[O:29])[CH:26]([CH3:28])[CH3:27])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 77264-ChlorobenzaldehydeHCID 774693,4-DifluoroanilineHCID 3017501Ethyl 5-methyl-2,4-dioxohexanoate

Product 1

HCID 896025365-(4-Chloro-phenyl)-1-(3,4-difluoro-phenyl)-3-hydroxy-4-isobutyryl-1,5-dihydro-pyrrol-2-oneYield 55.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3,4-difluoro-aniline (1.8 g, 14.2 mmol), 4-chloro-benzaldehyde (2.0 g, 14.2 mmol) and 5-methyl-2,4-dioxo-hexanoic acid ethyl ester (2.6 g, 14.2 mmol) acetic acid (10 mL) was refluxed overnight. The reaction mixture was allowed to cool to rt and diluted with acetonitrile. The resulting precipitate was collected by vacuum filtration and dried to afford 3.1 g of the title compound. tR: 5.89 min (HPLC 2); ESI-MS: 390 [M−H]− (LC-MS 2).

Workup

  1. temperaturewas refluxed overnight
  2. filtrationThe resulting precipitate was collected by vacuum filtration
  3. customdried

Sources & evidence

ORD record
ord-026d7c4f84ea4feea8948443ce7867ab
Source dataset
uspto-grants-2015_03
Patent number
US08969341B2

Reaction notes

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