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

HRID 218537

반응식

HRID 218537 반응식
[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

참가 물질

6

반응물 4

HCID 962WaterHCID 875934-Chloro-2-fluoro-5-nitrotolueneHCID 23665647Potassium tert-butoxideHCID 178426317HCID 178426317, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-babfbf2138ce4c39855e0fa8fe8bc918
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198267B2

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