Water → Methyl 3-formyl-1H-indole-7-carboxylate

HRID 971070

Reaction equation

HRID 971070 reaction equation
P(Cl)(Cl)(Cl)=O.[NH:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][C:13]=2[C:15]([O:17][CH3:18])=[O:16])[CH:8]=[CH:7]1.O.[OH-].[Na+].CN([CH:25]=[O:26])C>>[CH:25]([C:8]1[C:9]2[C:14](=[C:13]([C:15]([O:17][CH3:18])=[O:16])[CH:12]=[CH:11][CH:10]=2)[NH:6][CH:7]=1)=[O:26]

Participants

6

Reactant 5

HCID 962WaterHCID 6228Dimethylformamide2×HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 676694Methyl indole-7-carboxylate

Product 1

HCID 762965Methyl 3-formyl-1H-indole-7-carboxylate

Procedure

2.9 ml of phosphorus oxychloride are added slowly to 7 ml of N,N-dimethylformamide in a nitrogen atmosphere (formylation solution). 5 g (0.029 mol) of methyl indole-7-carboxylate are dissolved in 7 ml of DMF and added slowly to the formylation solution, during which the temperature does not rise above 30 degrees. The mixture is then warmed at 100° for one hour. After cooling, the mixture is poured into water and neutralised using sodium hydroxide solution, and the deposited crystals are filtered off with suction. m.p. 154°. Yield 5.3 g (89.9% of theory).

Workup

  1. additionadded slowly to the formylation solution, during which the temperature
  2. customdoes not rise above 30 degrees
  3. temperatureThe mixture is then warmed at 100° for one hour
  4. temperatureAfter cooling
  5. filtrationthe deposited crystals are filtered off with suction

Sources & evidence

ORD record
ord-76817f835db14e368bc637b54cebb03a
Source dataset
uspto-grants-2007_12
Patent number
US07312342B2

Linked notes

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