Methyl 2-methoxy-3-nitrobenzoate → Methyl 3-amino-2-methoxybenzoate

HRID 239345노트

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HRID 239345 반응식
[CH3:1][O:2][C:3]1[C:12]([N+:13]([O-])=O)=[CH:11][CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]>CO.[Ni]>[NH2:13][C:12]1[C:3]([O:2][CH3:1])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

참가 물질

4

반응물 1

HCID 590805Methyl 2-methoxy-3-nitrobenzoate

생성물 1

HCID 13338715Methyl 3-amino-2-methoxybenzoate수율 96.8%

시약·촉매·용매 2

HCID 935Nickel촉매HCID 887Methanol용매

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온도
25 °C

실험 절차

To a solution of methyl 2-methoxy-3-nitrobenzoate (28.4 g, 134 mmol) in MeOH (150 mL) was added Raney Ni (3 g). The mixture was stirred under H2 atmosphere (50 psi/25° C.) for 3.5 h. The catalyst was filtered, and the filtrate was concentrated under the reduced pressure to dryness to give the crude product, which was purified by recrystallization in EtOAc to afford the title compound of Step C, methyl 3-amino-2-methoxybenzoate (23.5 g, 96.4% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 6.80-6.93 (m, 3H), 5.10-5.25 (br, 2H), 3.78 (s, 3H), 3.67 (s, 3H).

후처리

  1. filtrationThe catalyst was filtered
  2. concentrationthe filtrate was concentrated under the reduced pressure to dryness
  3. customto give the crude product, which
  4. customwas purified by recrystallization in EtOAc

출처 및 근거

ORD 기록
ord-a9b25570149e482990561d59b622dd23
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642759B2

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