1,3-Cyclohexanedione → HCID 86733067, compound

HRID 918513Notes

Reaction equation

HRID 918513 reaction equation
[N:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=O)=[N+:2]=[N-:3].[C:12]1(=[O:19])[CH2:17][CH2:16][CH2:15][C:14](=O)[CH2:13]1.[CH2:20]([O:22][C:23](=[O:28])[CH2:24][C:25](=[NH:27])[NH2:26])[CH3:21]>C(O)C>[CH2:20]([O:22][C:23]([C:24]1[CH:6]([C:5]2[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=2[N:1]=[N+:2]=[N-:3])[C:13]2[C:12](=[O:19])[CH2:17][CH2:16][CH2:15][C:14]=2[NH:26][C:25]=1[NH2:27])=[O:28])[CH3:21]

Participants

5

Reactant 3

HCID 104341,3-CyclohexanedioneHCID 4599837Carbamimidoyl-acetic acid ethyl esterHCID 108880602-azidobenzaldehyde

Product 1

HCID 86733067HCID 86733067, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Upon heating a solution of 7.4 g of 2-azidobenzaldehyde, 5.6 g of cyclohexane-1,3-dione and 6.5 g of amidinoacetic acid ethyl ester in 100 ml of ethanol for 4 hours, 2-amino-4-(2-azidophenyl)-1,4,5,6,7,8-hexahydro-5-oxoquinoline-3-carboxylic acid ethyl ester of melting point 209°C (ethanol) is obtained. Yield: 58% of theory.

Sources & evidence

ORD record
ord-c5e7dba62b19459c8b95b544c691e72c
Source dataset
uspto-grants-1976_07
Patent number
US03971791

Reaction notes

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