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

HRID 1161884

반응식

HRID 1161884 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 23925Iron촉매HCID 702Ethanol용매

반응 조건

온도
85 °C

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-d5a07c42aa6c43d09299c5f96a3180f3
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07820672B2

연결된 노트

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