4-Nitro-3-(pyridin-3-ylmethoxy)-benzoic acid methyl ester → 4-Amino-3-(pyridin-3-ylmethoxy)-benzoic acid methyl ester

HRID 1821757노트

반응식

HRID 1821757 반응식
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[C:6]([O:13][CH2:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[CH:5]=1>CO.[Cl-].[NH4+].C(OCC)(=O)C.[Zn]>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([O:13][CH2:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[CH:5]=1

참가 물질

6

반응물 1

HCID 672560514-Nitro-3-(pyridin-3-ylmethoxy)-benzoic acid methyl ester

생성물 1

HCID 433801884-Amino-3-(pyridin-3-ylmethoxy)-benzoic acid methyl ester수율 97%

시약·촉매·용매 4

HCID 23994Zinc촉매HCID 887Methanol용매HCID 8857Ethyl Acetate용매HCID 25517Ammonium Chloride용매

실험 절차

To a stirred, cooled (about 0° C.) solution of 4-nitro-3-(pyridin-3-ylmethoxy)-benzoic acid methyl ester (288 mg, 1.0 mmol) in methanol (2 mL) and saturated aqueous ammonium chloride (1 mL) was added zinc dust (13.1 mg, 2.0 Mmol). After stirring for 12 hours, the reaction was diluted with 30 mL of ethyl acetate and washed with 30 mL of 10% aqueous sodium carbonate (2×30 mL), brine (1×30 mL), then dried (MgSO4), and filtered. The filtered solution was concentrated under reduced pressure to yield the desired product as a yellow solid (97% yield). 1H-NMR (400 MHz, CDCl3) δ 8.78 (s, 1H), 8.61 (d, 1H), 779 (d, 1H), 7.59 (m, 2H), 7.39 (m, 1H), 6.71 (d, 1H), 5.18 (s, 2H), 4.28 (br s, 2H), 3.85 (s, 3H).

후처리

  1. washwashed with 30 mL of 10% aqueous sodium carbonate (2×30 mL), brine (1×30 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationThe filtered solution was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-7ffd535fa5ad4b02a32f8eb6647da3ff
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07608618B2

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