Methyl formate → HCID 67855466, compound

HRID 483989Notes

Reaction equation

HRID 483989 reaction equation
[CH3:1][N:2]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:4]=1.[H-].[Na+].[CH:22](OC)=[O:23]>CN(C=O)C>[OH:23][CH:22]=[C:15]([N:2]([CH3:1])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:4]=1)[C:16]([O:18][CH3:19])=[O:17]

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-ca42a533aac04bc9b0699fda2ee9fbf1
Source dataset
uspto-grants-1993_07
Patent number
US05229393

Reaction notes

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