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

HRID 1161884

Reaction equation

HRID 1161884 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-d5a07c42aa6c43d09299c5f96a3180f3
Source dataset
uspto-grants-2010_10
Patent number
US07820672B2

Linked notes

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