Water → 1-(5-Chloro-2-methyl-4-nitrophenyl)-3-methylpyridin-2(1H)-one

HRID 218537

反応式

HRID 218537 の反応式
[OH:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][N:3]=1.CC(C)([O-])C.[K+].[Cl:15][C:16]1[CH:21]=[C:20](F)[C:19]([CH3:23])=[CH:18][C:17]=1[N+:24]([O-:26])=[O:25].O>CN(C=O)C>[Cl:15][C:16]1[C:17]([N+:24]([O-:26])=[O:25])=[CH:18][C:19]([CH3:23])=[C:20]([N:3]2[CH:4]=[CH:5][CH:6]=[C:7]([CH3:8])[C:2]2=[O:1])[CH:21]=1

参加物

6

反応物 4

HCID 962WaterHCID 875934-Chloro-2-fluoro-5-nitrotolueneHCID 23665647Potassium tert-butoxideHCID 178426317HCID 178426317、化合物

生成物 1

HCID 595866951-(5-Chloro-2-methyl-4-nitrophenyl)-3-methylpyridin-2(1H)-one

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

1.50 g (13.8 mmol) of 2-hydroxy-3-methylpyridine in 70 ml of DMF are admixed at 0° C. with 2.31 g (20.6 mmol) of potassium tert-butoxide, and the mixture is stirred at room temperature for 30 min. 2.87 g (15.1 mmol) of 2-chloro-4-fluoro-5-methylnitrobenzene are added while continuing to stir at RT. After 17 h, the mixture is admixed with 1000 ml of water and then extracted three times with ethyl acetate. The combined organic phases are dried over sodium sulfate and, after filtration, the solvents are removed under reduced pressure. The residue is purified by chromatography on silica gel (2:1 cyclohexane/ethyl acetate). This affords 2.15 g (56% of theory) of the desired compound.

後処理

  1. stirringto stir at RT
  2. waitAfter 17 h
  3. extractionextracted three times with ethyl acetate
  4. dry with materialThe combined organic phases are dried over sodium sulfate
  5. filtrationafter filtration
  6. customthe solvents are removed under reduced pressure
  7. customThe residue is purified by chromatography on silica gel (2:1 cyclohexane/ethyl acetate)

出典と根拠

ORDレコード
ord-babfbf2138ce4c39855e0fa8fe8bc918
出典データセット
uspto-grants-2012_06
特許番号
US08198267B2

関連ノート

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