Dimethylformamide → 3-formyl-2-methyl-1H-indole-5-carbonitrile

HRID 1015446Notes

Reaction equation

HRID 1015446 reaction equation
P(Cl)(Cl)(Cl)=O.CN(C)[CH:8]=[O:9].[CH3:11][C:12]1[NH:13][C:14]2[C:19]([CH:20]=1)=[CH:18][C:17]([C:21]#[N:22])=[CH:16][CH:15]=2.C(=O)([O-])[O-].[K+].[K+]>O>[CH:8]([C:20]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:21]#[N:22])[CH:18]=2)[NH:13][C:12]=1[CH3:11])=[O:9]

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 118296862-Methyl-1H-indole-5-carbonitrile

Product 1

HCID 866284803-formyl-2-methyl-1H-indole-5-carbonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under ice-cooling, 1.3 ml of phosphorus oxychloride was added to 7 ml of N,N-dimethylformamide at an inner temperature of from 10 to 20° C., followed by stirring at room temperature for 15 minutes. Under ice-cooling, 9 ml of an N,N-dimethylformamide solution of 2-methyl-1H-indole-5-carbonitrile was added to this solution at an inner temperature of from 10 to 20° C., followed by overnight stirring at room temperature. A 64 ml portion of water was added thereto at 0° C. and the pH was adjusted to 8 with potassium carbonate, followed by 2.5 hours of stirring at room temperature. The thus precipitated solid was collected by filtration, washed with water and then dried at 80° C. under a reduced pressure to obtain 1.73 g of 3-formyl-2-methyl-1H-indole-5-carbonitrile as a pale yellow solid.

Workup

  1. temperatureUnder ice-cooling
  2. temperatureUnder ice-cooling
  3. waitfollowed by overnight
  4. stirringstirring at room temperature
  5. customat 0° C.
  6. waitfollowed by 2.5 hours
  7. stirringof stirring at room temperature
  8. filtrationThe thus precipitated solid was collected by filtration
  9. washwashed with water
  10. customdried at 80° C. under a reduced pressure

Sources & evidence

ORD record
ord-7b17341874e2475db7fed2fef05deaaa
Source dataset
uspto-grants-2011_07
Patent number
US07985764B2

Reaction notes

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