Water → HCID 18946962, compound

HRID 1769205Notes

Reaction equation

HRID 1769205 reaction equation
[CH2:1]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][C:8]=2[C:14]([O:16][CH3:17])=[O:15])[CH2:2][CH2:3][CH3:4].[Cl:18]N1C(=O)CCC1=O.O>CN(C)C=O>[CH2:1]([C:5]1[NH:6][C:7]2[C:12]([C:13]=1[Cl:18])=[CH:11][CH:10]=[CH:9][C:8]=2[C:14]([O:16][CH3:17])=[O:15])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 18946596HCID 18946596, compound

Product 1

HCID 18946962HCID 18946962, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 2-(n-butyl)indole-7-carboxylate (32) (0.3 g) in 6 ml of dimethylformamide at room temperature was added N-chlorosuccinimide (0.17 g). The solution was stirred at room temperature for 16 hours, then water was added, and the mixture extracted with ether. The extract was separated and solvent evaporated under reduced pressure, to give methyl 2-(n-butyl)-3-chloroindole-7-carboxylate, a compound of Formula (33) where X is chloro, as an oil.

Workup

  1. extractionthe mixture extracted with ether
  2. customThe extract was separated
  3. customsolvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-dab49d1b988f4d4eb96ce28f0b661a0d
Source dataset
uspto-grants-1995_01
Patent number
US05380739

Reaction notes

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