1,3-Cyclohexanedione → HCID 70635761, compound

HRID 268071Notes

Reaction equation

HRID 268071 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH:5]=O)#[N:2].[C:11]1(=[O:18])[CH2:16][CH2:15][CH2:14][C:13](=O)[CH2:12]1.[CH2:19]([O:21][C:22](=[O:27])[CH2:23][C:24](=[NH:26])[NH2:25])[CH3:20]>C(O)C>[CH2:19]([O:21][C:22]([C:23]1[CH:5]([C:4]2[CH:7]=[CH:8][CH:9]=[CH:10][C:3]=2[C:1]#[N:2])[C:12]2[C:11](=[O:18])[CH2:16][CH2:15][CH2:14][C:13]=2[NH:25][C:24]=1[NH2:26])=[O:27])[CH3:20]

Participants

5

Reactant 3

HCID 104341,3-CyclohexanedioneHCID 1012092-CyanobenzaldehydeHCID 4599837Carbamimidoyl-acetic acid ethyl ester

Product 1

HCID 70635761HCID 70635761, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Upon heating a solution of 6.5 g of 2-cyanobenzaldehyde, 5.6 g of cyclohexane-1,3-dione and 6.5 g of amidinoacetic acid ethyl ester in 100 ml of ethanol for 5 hours, 2-amino-4-(2-cyanophenyl)-1,4,5,6,7,8-hexahydro-5-oxoquinoline-3-carboxylic acid ethyl ester of melting point 165°C (ethanol) is obtained.

Sources & evidence

ORD record
ord-2185f00a59a84529b296bfcd938657d4
Source dataset
uspto-grants-1976_03
Patent number
US03946026

Reaction notes

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