1,3-Cyclohexanedione → HCID 70635962, compound

HRID 918525Notes

Reaction equation

HRID 918525 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([CH:8]=O)[CH:5]=[CH:4][CH:3]=1.[C:10]1(=[O:17])[CH2:15][CH2:14][CH2:13][C:12](=O)[CH2:11]1.[CH2:18]([O:20][C:21](=[O:26])[CH2:22][C:23](=[NH:25])[NH2:24])[CH3:19].C(O)C.CN(C=O)C>C(O)C>[CH2:18]([O:20][C:21]([C:22]1[CH:8]([C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=2)[C:11]2[C:10](=[O:17])[CH2:15][CH2:14][CH2:13][C:12]=2[NH:24][C:23]=1[NH2:25])=[O:26])[CH3:19]

Participants

6

Reactant 4

HCID 104341,3-CyclohexanedioneHCID 707376-Methyl-2-pyridinecarboxaldehydeHCID 4599837Carbamimidoyl-acetic acid ethyl esterHCID 19794673N,N-dimethylformamide ethanol

Product 1

HCID 70635962HCID 70635962, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Upon heating a solution of 4.8 g of 6-methylpyridin-2-aldehyde, 4.5 g of cyclohexane-1,3-dione and 5.2 g of amidinoacetic acid ethyl ester in 120 ml of ethanol for 8 hours, 2-amino-4-(6-methylpyrid-2-yl)-1,4,5,6,7,8-hexahydro-5-oxoquinoline-3-carboxylic acid ethyl ester of melting point >260°C (ethanol/DMF) is obtained. Yield: 46% of theory.

Sources & evidence

ORD record
ord-3161d2d23ac34e0fb96425c9a4598c19
Source dataset
uspto-grants-1976_07
Patent number
US03971790

Reaction notes

Loading…