Water → Methyl 2-methoxy-3-nitrobenzoate

HRID 590116ノート

反応式

HRID 590116 の反応式
[OH:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:15]([O-])([O-])=O.[K+].[K+].IC.O>CN(C=O)C>[CH3:15][O:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

参加物

6

反応物 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 596904Methyl 2-hydroxy-3-nitrobenzoate

生成物 1

HCID 590805Methyl 2-methoxy-3-nitrobenzoate収率 98.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
45 °C

実験手順

To a solution of methyl 2-hydroxy-3-nitrobenzoate (26.8 g, 136 mmol) in DMF (200 mL) was added K2CO3 (61 g, 440 mmol). Then iodomethane (62 g, 436 mmol) was added dropwise to the mixture at rt. The mixture was stirred at 45° C. for 5 h. Then the mixture was cooled to rt and water was added. The reaction mixture was extracted with EtOAc (500 mL×2). The combined organic layers were washed with water successively, dried over Na2SO4, filtered and concentrated under reduced pressure to give the title compound of Step B (28.4 g, 98.8% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.10 (dd, J=1.8 Hz, 8.4 Hz, 1H), 8.00 (dd, J=1.3 Hz, 8.2 Hz, 1H), 7.40 (dd, J=8.2 Hz, 8.4 Hz, 1H), 3.87 (s, 3H), 3.85 (s, 3H).

後処理

  1. temperatureThen the mixture was cooled to rt
  2. extractionThe reaction mixture was extracted with EtOAc (500 mL×2)
  3. washThe combined organic layers were washed with water successively
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-4c59d534d64841868e8489ae3bbd24a9
出典データセット
uspto-grants-2016_01
特許番号
US09233956B2

反応ノート

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