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

HRID 568185

Reaction equation

HRID 568185 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>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

5

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 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

Procedure

Combine 2-carboethoxy-4,6-dichloroindole (20.0 g, 0.077 mol), and dimethylformamide (9.0 mL, 0.117 mol) in dichloroethane (100 mL). Add phosphoryl chloride (18.0 g, 0.117 mmol). Heat to reflux. After 3.5 hours, cool the reaction mixture to ambient temperature to obtain a solid. Collect the solid by filtration, rinse with water. Combine the solid with aqueous 1 M sodium acetate solution and stir. After 1 hour, filter, rinse with water, and dry to give 3-formyl-2-carboethoxy-4,6-dichloroindole.

Workup

  1. temperatureHeat to reflux
  2. customto obtain a solid
  3. customCollect the solid
  4. filtrationby filtration
  5. washrinse with water
  6. waitAfter 1 hour
  7. filtrationfilter
  8. washrinse with water
  9. customdry

Sources & evidence

ORD record
ord-e04611a419db4adc89247081133ddfb0
Source dataset
uspto-grants-2001_01
Patent number
US06180786B2

Linked notes

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