Benzoic acid, 4-hydroxy-3-nitro-, methyl ester → Methyl 3-amino-4-hydroxybenzoate

HRID 350367

반응식

HRID 350367 반응식
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-])=O>CO.[Pd]>[NH2:12][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:2]=1[OH:1])[C:6]([O:8][CH3:9])=[O:7]

참가 물질

4

반응물 1

HCID 66835Benzoic acid, 4-hydroxy-3-nitro-, methyl ester

생성물 1

HCID 10815Methyl 3-amino-4-hydroxybenzoate수율 69.4%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

A stirred mixture of methyl 4-hydroxy-3-nitrobenzoate (3.22 g, 0.0163 mol) and 5% Pd—C (12.9 g) in MeOH (30mL) was hydrogenated under an atmospheric pressure for 70 hr at room temp. Insoluble catalyst was removed, and the filtrate was evaporated in vacuo. The residue was chromatographed on silica-gel with EtOH—CHCl3 (1:20, v/v) as eluent to afford 1.89 g (69%) methyl 3-amino-4-hydroxybenzoate as a pale brown syrup.

후처리

  1. customInsoluble catalyst was removed
  2. customthe filtrate was evaporated in vacuo
  3. customThe residue was chromatographed on silica-gel with EtOH—CHCl3 (1:20, v/v) as eluent

출처 및 근거

ORD 기록
ord-795f063488d54799ad89dd33cb14ff31
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07179819B2

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