Acetic Acid → 4-Amino-5-chloro-2-methyl-indole-1-carboxylic acid methyl ester

HRID 1161884

反応式

HRID 1161884 の反応式
[CH3:1][O:2][C:3]([N:5]1[C:13]2[C:8](=[C:9]([N+:15]([O-])=O)[C:10]([Cl:14])=[CH:11][CH:12]=2)[CH:7]=[C:6]1[CH3:18])=[O:4].C(O)(=O)C.OS(O)(=O)=O>C(O)C.[Fe]>[CH3:1][O:2][C:3]([N:5]1[C:13]2[C:8](=[C:9]([NH2:15])[C:10]([Cl:14])=[CH:11][CH:12]=2)[CH:7]=[C:6]1[CH3:18])=[O:4]

参加物

6

反応物 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 668202645-Chloro-2-methyl-4-nitro-indole-1-carboxylic acid methyl ester

生成物 1

HCID 668199574-Amino-5-chloro-2-methyl-indole-1-carboxylic acid methyl ester

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 702Ethanol溶媒

反応条件

温度
85 °C

実験手順

5-Chloro-2-methyl-4-nitro-indole-1-carboxylic acid methyl ester (2.1 g, 7.81 mmol) is dissolved in ethanol (40 ml) and glacial acetic acid (40 ml). Iron powder (1.74 g, 31.26 mmol, activated previously with H2SO4 conc and then washed with water) is added, and the reaction mixture is heated to 85° C. for 90 minutes. The reaction mixture is poured into water and stirred at RT for 30 minutes, after which a slightly brownish colored precipitate forms which is filtered off. After washing with water and drying, the title compound is obtained in pure form. 1H NMR (DMSO, 400 MHz, 120° C.) δ 2.51 (s, 3H), 4.05 (s, 3H), 5.0-5.2 (br s, 2H), 6.66 (s, 1H), 7.05 (d, J=9 Hz, 1H), 7.31 (d, J=9 Hz, 1H); ES-MS: 238 [M+H]+.

後処理

  1. washwashed with water)
  2. additionis added
  3. additionThe reaction mixture is poured into water
  4. filtrationafter which a slightly brownish colored precipitate forms which is filtered off
  5. washAfter washing with water
  6. customdrying

出典と根拠

ORDレコード
ord-d5a07c42aa6c43d09299c5f96a3180f3
出典データセット
uspto-grants-2010_10
特許番号
US07820672B2

関連ノート

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