Benzaldehyde → 5-Methyl-7-phenyl-1,2,3,7-tetrahydroimidazolo[1,2-a]pyridine-6,8-dicarboxylic acid diethyl ester

HRID 1415309Notes

Reaction equation

HRID 1415309 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][C:14]([CH3:16])=O)[CH3:10].[C:18]([CH:23]=[C:24]1[NH:28][CH2:27][CH2:26][NH:25]1)([O:20][CH2:21][CH3:22])=[O:19]>C(O)C>[CH2:9]([O:11][C:12]([C:13]1[CH:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:23]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:24]2[NH:25][CH2:26][CH2:27][N:28]2[C:14]=1[CH3:16])=[O:17])[CH3:10]

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 8868Ethyl AcetoacetateHCID 12377942Ethyl (imidazolidin-2-ylidene)acetate

Product 1

HCID 681190295-Methyl-7-phenyl-1,2,3,7-tetrahydroimidazolo[1,2-a]pyridine-6,8-dicarboxylic acid diethyl esterYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Upon heating a solution of 5.3 g of benzaldehyde, 6.5 g of acetoacetic acid ethyl ester and 7.8 g of 2-carbethoxymethylideneimidazolidine in 50 ml of ethanol for 6 hours, 5-methyl-7-phenyl-1,2,3,7-tetrahydroimidazolo[1,2-a]pyridine-6,8-dicarboxylic acid diethyl ester of melting point 165° (alcohol) is obtained. Yield: 81% of theory.

Sources & evidence

ORD record
ord-d7f49fda0c644a54a82b7c13df7c0c48
Source dataset
uspto-grants-1977_01
Patent number
US04004015

Reaction notes

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