Dimethylformamide → HCID 12811136, compound

HRID 1155713Notes

Reaction equation

HRID 1155713 reaction equation
Cl.[CH3:2][C:3]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13]C(N)=[CH:11][CH:10]=2)[N:6]=[C:5]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:4]=1.C(=O)([O-])[O-].[K+].[K+].CI.[CH3:29][N:30]([CH3:33])[CH:31]=O>>[CH3:2][C:3]1[CH:8]=[C:7]([C:9]2[CH:10]=[CH:11][C:31]([N:30]([CH3:33])[CH3:29])=[CH:13][CH:14]=2)[N:6]=[C:5]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:4]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 12811134HCID 12811134, compound

Product 1

HCID 12811136HCID 12811136, compound

Conditions

Temperature
130 °C

Procedure

A mixture of ethyl 4-methyl-6-(4-aminophenyl)-2-pyridinecarboxylate hydrochloride (3.5 g), anhydrous potassium carbonate (8.8 g), dimethylformamide (30 ml) and methyl iodide (10 ml) is agitated at 50° C. for 30 minutes and further at 130° C. for 3 hours. After cooling, the reaction mixture is filtered to remove potassium carbonate. The filtrate is concentrated under reduced pressure in order to distill off the solvent. To the resulting residue is added water, and the mixture is extracted with ethyl acetate. The extract is washed with water and dried, and ethyl acetate is distilled off to give ethyl 4-methyl-6-(4-dimethylaminophenyl)-2-pyridinecarboxylate (2.2 g). M.P. 143°-144° C.

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture is filtered
  3. customto remove potassium carbonate
  4. concentrationThe filtrate is concentrated under reduced pressure in order
  5. distillationto distill off the solvent
  6. additionTo the resulting residue is added water
  7. extractionthe mixture is extracted with ethyl acetate
  8. washThe extract is washed with water
  9. customdried
  10. distillationethyl acetate is distilled off

Sources & evidence

ORD record
ord-46c02786a6c14051a41b76f76514a9e1
Source dataset
uspto-grants-1982_06
Patent number
US04332809

Reaction notes

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