Chlorosuccinimide → ethyl 3-chloro-1H-indole-2-carboxylate

HRID 453869Notes

Reaction equation

HRID 453869 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([O:12][CH2:13][CH3:14])=[O:11].C1C(=O)N([Cl:22])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Cl:22][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][C:2]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 73125Ethyl indole-2-carboxylate

Product 1

HCID 13329562ethyl 3-chloro-1H-indole-2-carboxylateYield 73%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Ethyl 1H-indole-2-carboxylate (26.45 mmol, 1.0 equiv.) was dissolved in CCl4 (26 ml); NCS (29.10 mmol, 1.1 equiv.) was added and the mixture was heated for 16 h at boiling temperature. The resulting solid was filtered out, and the filtrate was washed with water (2×50 ml) and sat. NaCl solution (50 ml), dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by column chromatography (10% ethyl acetate in hexane). Yield: 73%

Workup

  1. temperaturethe mixture was heated for 16 h
  2. filtrationThe resulting solid was filtered out
  3. washthe filtrate was washed with water (2×50 ml) and sat. NaCl solution (50 ml)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by column chromatography (10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-1303256fd9f64009bd2f74afa1f7fe53
Source dataset
uspto-grants-2013_07
Patent number
US08492559B2

Reaction notes

Loading…