Carbon Tetrachloride → Methyl 2,3,4,9-tetrahydro-1-oxo-1H-carbazole-7-carboxylate

HRID 278087Notes

Reaction equation

HRID 278087 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][C:7]1[C:15]2[C:10](=[CH:11][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:14]=2)[NH:9][CH:8]=1)([OH:3])=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>ClCCCl.C(Cl)(Cl)Cl>[O:3]=[C:1]1[C:8]2[NH:9][C:10]3[CH:11]=[C:12]([C:16]([O:18][CH3:19])=[O:17])[CH:13]=[CH:14][C:15]=3[C:7]=2[CH2:6][CH2:5][CH2:4]1

Participants

6

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 22627515HCID 22627515, compound

Product 1

HCID 13626581Methyl 2,3,4,9-tetrahydro-1-oxo-1H-carbazole-7-carboxylateYield 44.8%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6212ChloroformSolvent

Procedure

A mixture or methyl 3-(3-carboxypropyl)indole-6-carboxylate (173 mg), triphenylphosphine (191 mg) and carbon tetrachloride (1.0 ml) in 1,2-dichloroethane (10 ml) was heated at 80° C. for 2 hours. The resulting mixture was diluted with chloroform and washed with water, aqueous sodium bicarbonate and brine. The organic phase was dried over sodium sulfate and evaporated in vacuo. The residue was purified by silica gel thin layer chromatography with a mixture of hexane and ethyl acetate (4:1) and recrystallized from a mixture of hexane and ethyl acetate to give methyl 8-oxo-5,6,7,8-tetrahydrocarbazole-2-carboxylate (72.2 mg) as colorless crystals.

Workup

  1. washwashed with water, aqueous sodium bicarbonate and brine
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. customevaporated in vacuo
  4. customThe residue was purified by silica gel thin layer chromatography with a mixture of hexane and ethyl acetate (4:1)
  5. customrecrystallized from a mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-0e3a429183094eefa097d2549af3e86e
Source dataset
uspto-grants-2002_03
Patent number
US06358992B1

Reaction notes

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