Ethyl (imidazolidin-2-ylidene)acetate → 5-Methyl-7-(naphth-1-yl)-1,2,3,7-tetrahydroimidazolo[1,2-a]pyridine-6,8-dicarboxylic acid diethyl ester

HRID 972882Notes

Reaction equation

HRID 972882 reaction equation
C(O[C:4](=O)[CH2:5][C:6]([CH:8]=[C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH2:10]1)=O)C.[C:20]([CH:25]=[C:26]1[NH:30][CH2:29][CH2:28][NH:27]1)([O:22][CH2:23][CH3:24])=[O:21]>C(O)C>[CH2:23]([O:22][C:20]([C:6]1[CH:8]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[CH:11][CH:10]=2)[C:25]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:26]2[NH:27][CH2:28][CH2:29][N:30]2[C:5]=1[CH3:4])=[O:21])[CH3:24]

Participants

4

Reactant 2

HCID 12377942Ethyl (imidazolidin-2-ylidene)acetateHCID 70607594(1-Naphthylidene)acetoacetic acid ethyl ester

Product 1

HCID 681193055-Methyl-7-(naphth-1-yl)-1,2,3,7-tetrahydroimidazolo[1,2-a]pyridine-6,8-dicarboxylic acid diethyl esterYield 52%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Heating a solution of 9.0 g of (naphth-1-ylidene)acetoacetic acid ethyl ester and 5.2 g of 2-carbethoxymethylideneimidazolidine in 60 ml of ethanol for 6 hours yields 5-methyl-7-(naphth-1-yl)-1,2,3,7-tetrahydroimidazolo[1,2-a]pyridine-6,8-dicarboxylic acid diethyl ester of melting point 169° - 170° C. (ethanol).

Sources & evidence

ORD record
ord-9655111bbe2347558518815f45e58c98
Source dataset
uspto-grants-1977_10
Patent number
US04053614

Reaction notes

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