Methyl chloroformate → 5-Chloro-2-methyl-4-nitro-indole-1-carboxylic acid methyl ester

HRID 1161883Notes

Reaction equation

HRID 1161883 reaction equation
[Cl:1][C:2]1[C:3]([N+:12]([O-:14])=[O:13])=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH3:11])=[CH:5]2.[H-].[Na+].Cl[C:18]([O:20][CH3:21])=[O:19]>CN(C=O)C>[CH3:21][O:20][C:18]([N:7]1[C:8]2[C:4](=[C:3]([N+:12]([O-:14])=[O:13])[C:2]([Cl:1])=[CH:10][CH:9]=2)[CH:5]=[C:6]1[CH3:11])=[O:19]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 24758Sodium hydrideHCID 668200375-Chloro-2-methyl-4-nitro-1H-indole

Product 1

HCID 668202645-Chloro-2-methyl-4-nitro-indole-1-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Chloro-2-methyl-4-nitro-1H-indole (1.62 g, 7.69 mmol) is dissolved under an atmosphere of argon in dry DMF (30 ml). After addition of a NaH suspension (60% in mineral oil, 369 mg, 9.22 mmol) the mixture is stirred for 1 hour at RT. Methyl chloroformate (0.72 ml, 9.22 mmol) is added slowly during 10 minutes, and the reaction mixture is stirred at RT for 1 hour to form a yellowish suspension. After filtration and drying, the title compound is obtained in pure form. 1H NMR (DMSO, 400 MHz) δ 2.53 (s, 3H), 4.06 (s, 3H), 6.71 (s, 1H), 7.57 (d, J=9.0 Hz, 1H), 8.30 (d, J=9.0 Hz, 1H); ES-MS: 268 [M+H]+.

Workup

  1. stirringthe reaction mixture is stirred at RT for 1 hour
  2. customto form a yellowish suspension
  3. filtrationAfter filtration
  4. customdrying

Sources & evidence

ORD record
ord-fc1c12835264404eabaffc2efaa5ba23
Source dataset
uspto-grants-2010_10
Patent number
US07820672B2

Reaction notes

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