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

HRID 1976782

Reaction equation

HRID 1976782 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[Cl:14]N1C(=O)CCC1=O>CO>[Cl:14][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[C:6]([C:10]([O:12][CH3:13])=[O:11])[CH:5]=2)[NH:1][CH:2]=1

Participants

4

Reactant 2

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

Product 1

HCID 219987283-Chloro-1H-indole-5-carboxylic acid methyl esterYield 66.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 5-indolecarboxylate (501.1 mg, 2.65 mmol) in methanol (15 mL) was treated with N-chlorosuccinimide (425.4 mg, 3.18 mmol), stirred for 18 hours, and concentrated. The concentrate was dissolved into ethyl acetate, and this solution was washed with 1M NaHCO3 (2×), dried (MgSO4), filtered, and concentrated. The concentrate was purified on silica gel with 15% ethyl acetate/hexanes to provide 368.8 mg of the desired product.

Workup

  1. concentrationconcentrated
  2. dissolutionThe concentrate was dissolved into ethyl acetate
  3. washthis solution was washed with 1M NaHCO3 (2×)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe concentrate was purified on silica gel with 15% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-932d88836c234f719928692ef1000938
Source dataset
uspto-grants-2001_05
Patent number
US06228868B1

Linked notes

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