Dimethylformamide → ethyl 4,6-dichloro-3-formyl-1H-indole-2-carboxylate

HRID 864523Notes

Reaction equation

HRID 864523 reaction equation
[C:1]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[C:12]([Cl:15])[CH:11]=[C:10]([Cl:16])[CH:9]=2)([O:3][CH2:4][CH3:5])=[O:2].CN(C)[CH:19]=[O:20].P(Cl)(Cl)(Cl)=O.C([O-])(=O)C.[Na+]>ClC(Cl)C>[CH:19]([C:14]1[C:13]2[C:8](=[CH:9][C:10]([Cl:16])=[CH:11][C:12]=2[Cl:15])[NH:7][C:6]=1[C:1]([O:3][CH2:4][CH3:5])=[O:2])=[O:20]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 517045Sodium AcetateHCID 2736407ethyl 4,6-dichloro-1H-indole-2-carboxylate

Product 1

HCID 2794948ethyl 4,6-dichloro-3-formyl-1H-indole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

Combine 2-carboethoxy-4,6-dichloroindole (10.0 g, 0.039 mol), and dimethylformamide (4.5 mL, 0.057 mol) in dichloroethane (20 mL). Add phosphoryl chloride (8.9 g, 0.058 mmol). Heat to 80° C. After 18 hours, cool the reaction mixture to ambient temperature and combine with aqueous 1M sodium acetate solution and stir. After 18 hours, filter, rinse with water, and dry to give 3-formyl-2-carboethoxy-4,6-dichloroindole.

Workup

  1. temperaturecool the reaction mixture to ambient temperature
  2. waitAfter 18 hours
  3. filtrationfilter
  4. washrinse with water
  5. customdry

Sources & evidence

ORD record
ord-51a6aabf800c4a3dadbf46084a29b257
Source dataset
uspto-grants-1996_10
Patent number
US05563157

Reaction notes

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