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

HRID 902870Notes

Reaction equation

HRID 902870 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-ae7801daffb54c579f38bd06365872a5
Source dataset
uspto-grants-2008_04
Patent number
US07365205B2

Reaction notes

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