Phosphorus oxychloride → ethyl 5-chloro-3-formyl-1H-indole-2-carboxylate

HRID 1392764Notes

Reaction equation

HRID 1392764 reaction equation
P(Cl)(Cl)(Cl)=O.CN([CH:14]=[O:15])C1C=CC=CC=1.[Cl:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][C:21]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:20]2.C([O-])(=O)C.[Na+]>ClCCCl>[Cl:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][C:21]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:20]2[CH:14]=[O:15]

Participants

6

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 66737N-MethylformanilideHCID 78518Ethyl 5-chloroindole-2-carboxylateHCID 517045Sodium Acetate

Product 1

HCID 4410568ethyl 5-chloro-3-formyl-1H-indole-2-carboxylateYield 79.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

After phosphorus oxychloride (2.0 ml) was added to N-methylformanilide (2.9 g), and the mixture was stirred for 15 minutes, 1,2-dichloroethane (50 ml) and ethyl 5-chloroindole-2-carboxylate (4.0 g) were added, and the resultant mixture was heated under reflux for 1 hour. The reaction mixture was poured into an aqueous solution (28 ml) of sodium acetate (14 g) under ice cooling. After stirring for 18 hours, insoluble matter was collected by filtration. This product was successively washed with water and diethyl ether to obtain the title compound (3.56 g).

Workup

  1. temperatureunder reflux for 1 hour
  2. stirringAfter stirring for 18 hours
  3. filtrationinsoluble matter was collected by filtration
  4. washThis product was successively washed with water and diethyl ether

Sources & evidence

ORD record
ord-dfe73ba6ac7b4da7a3dcddd38547c7eb
Source dataset
uspto-grants-2008_03
Patent number
US07342014B2

Reaction notes

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