Benzaldehyde → Ethyl alpha-dimethylaminocinnamate

HRID 1085841

Reaction equation

HRID 1085841 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:9]([O:11][C:12](=[O:17])[CH2:13][N:14]([CH3:16])[CH3:15])[CH3:10].[H-].[Na+].C(O)C>CCOCC>[CH3:15][N:14]([CH3:16])[C:13](=[CH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:12]([O:11][CH2:9][CH3:10])=[O:17]

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 702EthanolHCID 24758Sodium hydrideHCID 118412Glycine, N,N-dimethyl-, ethyl ester

Product 1

HCID 708380Ethyl alpha-dimethylaminocinnamateYield 60%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Benzaldehyde, N,N-dimethylglycine ethyl ester and sodium hydride were reacted in ether with the addition of a catalytic amount of ethanol according to the method described in Lieb. Ann. Chem. 703 (1967) 37°-43 to give ethyl α-dimethylaminocinnamate. This compound was then reacted according to the method described in Tetrahedron Letters, 46, (1978) 4573°-4574 with oxalyl chloride and hydrazine in 60% yield to give ethyl 4-phenyl-3-pyrazolecarboxylate, melting point 164°-165° after recrystallization from ethanol/diethyl ether.

Sources & evidence

ORD record
ord-42ce2aa473b54529ba07510feaec3441
Source dataset
uspto-grants-1991_04
Patent number
US05011849

Linked notes

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