Methyl formate → HCID 67855466, compound

HRID 1381465Notes

Reaction equation

HRID 1381465 reaction equation
[CH3:1][O:2][C:3](=[O:19])[CH2:4][N:5]([CH3:18])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=1.[H-].[Na+].[CH:22](OC)=[O:23]>CN(C=O)C>[OH:23][CH:22]=[C:4]([N:5]([CH3:18])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=1)[C:3]([O:2][CH3:1])=[O:19]

Participants

5

Reactant 3

HCID 7865Methyl formateHCID 24758Sodium hydrideHCID 21275949HCID 21275949, compound

Product 1

HCID 67855466HCID 67855466, compoundYield 12.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl(N-methyl-3-phenylanilino)acetate (4.33 g) was formylated as described in Example 1 by treatment with sodium hydride (0.94 g) and methyl formate (21.01 g) in DMF (50 ml) to give methyl 3-hydroxy-2-(N-methyl-3'-phenylanilino)propenoate (0.60 g) as a brown viscous liquid. Methylation with dimethyl sulphate (0.59 g) and potassium carbonate (0.62 g) in DMF (25 ml) for 5 hours afforded on work-up and HPLC (eluent petroleum ether-ether, 70:30) on silica gel a pure sample of the title compound (260 mg) as a yellow liquid.

Sources & evidence

ORD record
ord-50dd7233b04540ddba7afe4ca2dec57d
Source dataset
uspto-grants-1989_02
Patent number
US04802913

Reaction notes

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