Dimethylformamide → Methyl 3-formyl-1H-indole-5-carboxylate

HRID 1015438Notes

Reaction equation

HRID 1015438 reaction equation
P(Cl)(Cl)(Cl)=O.CN(C)[CH:8]=[O:9].[NH:11]1[C:19]2[C:14](=[CH:15][C:16]([C:20]([O:22][CH3:23])=[O:21])=[CH:17][CH:18]=2)[CH:13]=[CH:12]1.C(=O)([O-])[O-].[K+].[K+]>O>[CH:8]([C:13]1[C:14]2[C:19](=[CH:18][CH:17]=[C:16]([C:20]([O:22][CH3:23])=[O:21])[CH:15]=2)[NH:11][CH:12]=1)=[O:9]

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 2737635methyl 1H-indole-5-carboxylate

Product 1

HCID 19606277Methyl 3-formyl-1H-indole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 1.28 ml portion of phosphoryl chloride was added dropwise to 8 ml of N,N-dimethylformamide under ice-cooling, followed by stirring at room temperature for 15 minutes. An 8 ml portion of an N,N-dimethylformamide solution of 2.00 g of methyl 1H-indole-5-carboxylate was added dropwise to this solution under ice-cooling, followed by stirring at room temperature for 1.5 hours. Under ice-cooling, 50 ml of water was added thereto and potassium carbonate was further added until the pH became 12, and the resulting solid was collected by filtration, washed with water and then dried over heating under a reduced pressure to obtain 2.19 g of methyl 3-formyl-1H-indole-5-carboxylate as a pale light brown solid.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringby stirring at room temperature for 1.5 hours
  4. temperatureUnder ice-cooling
  5. filtrationthe resulting solid was collected by filtration
  6. washwashed with water
  7. customdried
  8. temperatureover heating under a reduced pressure

Sources & evidence

ORD record
ord-a132fc67bde94ce19325d24809f21901
Source dataset
uspto-grants-2011_07
Patent number
US07985764B2

Reaction notes

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