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

HRID 568187

Reaction equation

HRID 568187 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 1 M 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-e8efce8ed6ef48ca829ab6cf28d56553
Source dataset
uspto-grants-2001_01
Patent number
US06180786B2

Linked notes

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