Chlorosuccinimide → 3-Chloro-1H-indole-6-carboxylic acid

HRID 842393Notes

Reaction equation

HRID 842393 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([OH:12])=[O:11])[CH:8]=2)[CH:3]=[CH:2]1.[Cl:13]N1C(=O)CCC1=O>ClCCl.CN(C=O)C>[Cl:13][C:3]1[C:4]2[C:9](=[CH:8][C:7]([C:10]([OH:12])=[O:11])=[CH:6][CH:5]=2)[NH:1][CH:2]=1

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 5952301H-indole-6-carboxylic acid

Product 1

HCID 155430423-Chloro-1H-indole-6-carboxylic acidYield 80%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of indole-6-carboxylic acid (2.45 g, 15.2 mmol) in dichloromethane (100 mL) and DMF (10 mL) was added N-chlorosuccinimide (2 g, 15.2 mmol). After 3 h, the solvent was removed in vacuo and the residue was suspended in dichloromethane, sonicated and filtered to give 2.38 g (80%) of the title compound.

Workup

  1. customthe solvent was removed in vacuo
  2. customsonicated
  3. filtrationfiltered

Sources & evidence

ORD record
ord-63a6b74051dd46d4894513e8c19e6d49
Source dataset
uspto-grants-2002_04
Patent number
US06372759B1

Reaction notes

Loading…