Dimethylformamide → HCID 12811145, compound

HRID 1155717Notes

Reaction equation

HRID 1155717 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12]C(N)=[CH:10][CH:9]=2)[N:5]=[C:4]([C:15]([O:17][CH3:18])=[O:16])[CH:3]=1.CI.[C:21](=O)([O-])[O-].[K+].[K+].[CH3:27][N:28]([CH3:31])[CH:29]=O>O>[CH3:21][O:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:29]([N:28]([CH3:31])[CH3:27])=[CH:10][CH:9]=2)[N:5]=[C:4]([C:15]([O:17][CH3:18])=[O:16])[CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178498549HCID 178498549, compound

Product 1

HCID 12811145HCID 12811145, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl 4-hydroxy-6-(4-aminophenyl)-2-pyridinecarboxylate (1.22 g), methyl iodide (3.82 g), potassium carbonate (2.76 g), dimethylformamide (20 ml) and water (1 ml) is agitated at room temperature for 3 hours. The reaction mixture is concentrated under reduced pressure, and to the residue is added water. The precipitated crystals are collected by filtration and dissolved in chloroform. The solution is passed through a column packed with silica gel (30 g). The solution passed through the column is concentrated to remove the solvent to give methyl 4-methoxy-6-(4-dimethylaminophenyl)-2-pyridinecarboxylate (0.74 g). M.P. 157°-158° C.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. additionto the residue is added water
  3. filtrationThe precipitated crystals are collected by filtration
  4. dissolutiondissolved in chloroform
  5. concentrationis concentrated
  6. customto remove the solvent

Sources & evidence

ORD record
ord-8b8a6861a9ad4ce3a9663a7f6e770753
Source dataset
uspto-grants-1982_06
Patent number
US04332809

Reaction notes

Loading…