Potassium Carbonate → Ethyl 5-acetoxy-3-chloroindole-2-carboxylate

HRID 1582635Notes

Reaction equation

HRID 1582635 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:8]2)(=[O:3])[CH3:2].[Cl:19]N1C(=O)CCC1=O.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[C:1]([O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:8]2[Cl:19])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 31398ChlorosuccinimideHCID 11379620Ethyl 5-acetoxyindole-2-carboxylate

Product 1

HCID 22718726Ethyl 5-acetoxy-3-chloroindole-2-carboxylateYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl 5-acetoxyindole-2-carboxylate (500 mg) in dichloromethane (10 ml) was stirred at room temperature in the presence of N-chlorosuccinimide (297 mg) and potassium carbonate (279 mg) overnight. The resulting precipitate was collected by filtration, washed with cold dichloromethane followed by water and dried under vacuum overnight to give the desired product as a white powder (425 mg, 75%). NMR: δ 1.35 (t,3H), 2.25 (s,3H), 4.4 (q,2H), 7.1 (d,1H), 7.3 (s, 1H), 7.5 (d, 1H), 12.2 (s, 1H); m/z 281.9 (M+H+).

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed with cold dichloromethane
  3. customdried under vacuum overnight

Sources & evidence

ORD record
ord-1574cdbe04cc4f9ea27343222f2f1b7b
Source dataset
uspto-grants-2004_05
Patent number
US06737435B1

Reaction notes

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