1,3-Cyclohexanedione → HCID 86734361, compound

HRID 1414421Notes

Reaction equation

HRID 1414421 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)C=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])N)[CH3:20].[CH2:28](O)C.CN(C)C=O>C(O)C>[CH2:19]([O:21][C:22]([C:23]1[CH2:28][C:12]2[C:11](=[O:18])[CH2:16][CH2:15][CH2:14][C:13]=2[N:26]([C:5]2[CH:8]=[CH:9][CH:10]=[C:3]([C:1]#[N:2])[CH:4]=2)[CH:24]=1)=[O:27])[CH3:20]

Participants

6

Reactant 4

HCID 104341,3-CyclohexanedioneHCID 90670m-FormylbenzonitrileHCID 4599837Carbamimidoyl-acetic acid ethyl esterHCID 19794673N,N-dimethylformamide ethanol

Product 1

HCID 86734361HCID 86734361, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Heating a solution of 6.5 g of 3-cyanobenzaldehyde, 5.6 g of cyclohexane-1,3-dione and 6.5 g of amidinoacetic acid ethyl ester in 100 ml of ethanol for 6 hours yields 2-amino-4-((3-cyanophenyl)-1,4,5,6,7,8-hexahydro-5-oxoquinoline-3-carboxylic acid ethyl ester of melting point 262°C (ethanol/dimethylformamide).

Sources & evidence

ORD record
ord-dd0cbd2c7c32437e83fffc5448edbf53
Source dataset
uspto-grants-1977_01
Patent number
US04001258

Reaction notes

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