Water → 2-{[2-Methyl-3-(methyloxy)phenyl]oxy}-5-nitropyridine

HRID 1023549노트

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HRID 1023549 반응식
[CH3:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:10].[H-].[Na+].Cl[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][N:15]=1.O>CN(C=O)C>[CH3:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=1[O:10][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][N:15]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 783082-Chloro-5-nitropyridineHCID 2489133-Methoxy-2-methylphenol2회

생성물 1

HCID 672360642-{[2-Methyl-3-(methyloxy)phenyl]oxy}-5-nitropyridine수율 93.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
60 °C

실험 절차

To a solution of 2-methyl-3-(methyloxy)phenol (Intermediate 59, 1.3 g) in DMF (50 mL) was added sodium hydride (60% in mineral oil, 480 mg, 0.012 mol at 0° C. and the mixture was stirred for 30 minutes. 2-Chloro-5-nitropyridine (1.9 g, 0.012 mol, Aldrich) was added and the mixture was heated at 60° C. for 3 hours. The mixture was poured into H2O (100 mL) and extracted with ethyl acetate (4 times 100 mL). The combined ethyl acetate phases were dried over sodium sulphate and concentrated under vacuum to give a residue which was purified by column chromatography on silica gel (PE:EtOAc=10:1) to afford the title compound (2.3 g) as a liquid.

후처리

  1. extractionextracted with ethyl acetate (4 times 100 mL)
  2. dry with materialThe combined ethyl acetate phases were dried over sodium sulphate
  3. concentrationconcentrated under vacuum
  4. customto give a residue which
  5. customwas purified by column chromatography on silica gel (PE:EtOAc=10:1)

출처 및 근거

ORD 기록
ord-dd083a2e76ed46df86c23639955836eb
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722695B2

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