Water → Methyl 2-methoxy-3-nitrobenzoate

HRID 239344노트

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HRID 239344 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 590805Methyl 2-methoxy-3-nitrobenzoate수율 98.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
45 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-7109187ff9144c958e485138feaa5764
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642759B2

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