Dimethylformamide → Methyl 2-(4-dimethylaminophenyl)benzofuran-7-carboxylate

HRID 1761910Notes

Reaction equation

HRID 1761910 reaction equation
NC1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=[CH:13][C:11]=3[CH:12]=2)=[CH:4][CH:3]=1.CI.C(=O)([O-])[O-].[K+].[K+].[CH3:29][N:30]([CH3:33])[CH:31]=O>O>[CH3:29][N:30]([CH3:33])[C:31]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=[CH:13][C:11]=3[CH:12]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodide2×HCID 11430Potassium CarbonateHCID 14229714Methyl 2-(4-aminophenyl)benzofuran-7-carboxylate

Product 1

HCID 14229715Methyl 2-(4-dimethylaminophenyl)benzofuran-7-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2.6 g of methyl 2-(4-aminophenyl)benzofuran-7-carboxylate, 1.52 ml of methyl iodide, 6.72 g of potassium carbonate and 25 ml of dimethylformamide is stirred at room temperature for 1 hour. 2.2 ml of methyl iodide are added to the mixture and the mixture is stirred for 2 hours. The reaction mixture is poured into water and the aqueous mixture is extracted with ethyl acetate. The extract is washed with water, dried and evaporated to remove solvent. The residue is purified by silica gel column chromatography (solvent; n-hexane:ethyl acetate=1:4) to give 2.0 g of methyl 2-(4-dimethylaminophenyl)benzofuran-7-carboxylate as orange needles.

Workup

  1. stirringthe mixture is stirred for 2 hours
  2. extractionthe aqueous mixture is extracted with ethyl acetate
  3. washThe extract is washed with water
  4. customdried
  5. customevaporated
  6. customto remove solvent
  7. customThe residue is purified by silica gel column chromatography (solvent; n-hexane:ethyl acetate=1:4)

Sources & evidence

ORD record
ord-9fbb6765ace3429daea608f1c4a218a9
Source dataset
uspto-grants-1989_05
Patent number
US04829067

Reaction notes

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