Water → HCID 12799961, compound

HRID 2412641Notes

Reaction equation

HRID 2412641 reaction equation
P(Cl)(Cl)(Cl)=O.[CH2:6]([C:17]1[NH:18][C:19]2[C:24]([CH:25]=1)=[CH:23][C:22]([C:26]([O:28][CH3:29])=[O:27])=[CH:21][CH:20]=2)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].O.[OH-].[Na+].CN(C)[CH:35]=[O:36]>C(O)(=O)C>[CH:35]([C:25]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([C:26]([O:28][CH3:29])=[O:27])[CH:23]=2)[NH:18][C:17]=1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[O:36]

Participants

7

Reactant 5

HCID 962WaterHCID 6228Dimethylformamide2×HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 12799921HCID 12799921, compound

Product 1

HCID 12799961HCID 12799961, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of phosphorus oxychloride (21.5 ml) in dimethylformamide (80 ml) was added to a solution of methyl 2-(n-undecyl)indole-5-carboxylate (36.9 g) in dimethylformamide (320 ml) and the mixture was stirred at a temperature of 60°-70° C. for 2 hours. After cooling the mixture was poured into water (500 ml). An aqueous solution of sodium hydroxide (50% w/v) was added to the mixture to adjust the pH to 12. Glacial acetic acid was then added to the stirred mixture to readjust the pH to 5. The resultant solid was collected and on recrystallisation from ethanol gave methyl 3-formyl-2-(n-undecyl)indole-5-carboxylate (34.8 g), m.p. 162°-165° C.

Workup

  1. temperatureAfter cooling the mixture
  2. customThe resultant solid was collected and on recrystallisation from ethanol

Sources & evidence

ORD record
ord-d45534f7be464423befcadd6dbabbe4f
Source dataset
uspto-grants-1985_01
Patent number
US04493843

Reaction notes

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