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

HRID 582050Notes

Reaction equation

HRID 582050 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 dichloromethane. Combine the solid with aqueous 1 M sodium acetate solution and stir. After 1 hour, filter, rinse with water, and dry to give the title compound.

Workup

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

Sources & evidence

ORD record
ord-6b2b2b94f1cc4357a5f482b64dff5fa0
Source dataset
uspto-grants-1999_07
Patent number
US05922752

Reaction notes

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