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

HRID 1830741ノート

反応式

HRID 1830741 の反応式
[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

参加物

6

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 23994Zinc触媒HCID 887Methanol溶媒HCID 8857Ethyl Acetate溶媒HCID 25517Ammonium Chloride溶媒

実験手順

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 (131 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) δ8.78 (s, 1H), 8.61 (d, 1H, 7.79 (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).

後処理

  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

出典と根拠

ORDレコード
ord-eee3ec3d0c7044db88546e4262adb969
出典データセット
uspto-grants-2006_06
特許番号
US07067506B2

反応ノート

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