Chlorosuccinimide → 3-Chloro-1H-indole-5-carboxylic acid methyl ester

HRID 2113468

Reaction equation

HRID 2113468 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH:9]=[CH:8]2)=[O:4].[Cl:14]N1C(=O)CCC1=O>CO>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH:9]=[C:8]2[Cl:14])=[O:4]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 2737635methyl 1H-indole-5-carboxylate

Product 1

HCID 219987283-Chloro-1H-indole-5-carboxylic acid methyl esterYield 62.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1.4 g (8 mmol) 1H-indole-5-carboxylic acid methyl ester and 1.28 g (9.6 mmol) N-chlorosuccinimid in 40 mL methanol was stirred at room temperature for 16 h. The mixture was evaporated to dryness and taken up in DCM washed with 1N NaHCO3 aq, dried with MgSO4, filtered and evaporated to dryness to yield 1.05 g (62%) of the title compound. MS(m/e): 210.1 (MH+).

Workup

  1. customThe mixture was evaporated to dryness
  2. washwashed with 1N NaHCO3 aq
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-3b5c17169e574e9a83ea3a80bfdc003e
Source dataset
uspto-grants-2008_10
Patent number
US07432255B2

Linked notes

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