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

HRID 1023549ノート

反応式

HRID 1023549 の反応式
[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

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 783082-Chloro-5-nitropyridineHCID 2489133-Methoxy-2-methylphenol2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-dd083a2e76ed46df86c23639955836eb
出典データセット
uspto-grants-2014_05
特許番号
US08722695B2

反応ノート

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