1,3-Cyclohexanedione → HCID 70635419, compound

HRID 268072Notes

Reaction equation

HRID 268072 reaction equation
[N+:1]([C:4]1[C:9]([CH:10]=O)=[CH:8][C:7]([O:12][CH3:13])=[C:6]([O:14][CH3:15])[CH:5]=1)([O-:3])=[O:2].[C:16]1(=[O:23])[CH2:21][CH2:20][CH2:19][C:18](=O)[CH2:17]1.[CH2:24]([O:26][C:27](=[O:32])[CH2:28][C:29](=[NH:31])[NH2:30])[CH3:25]>C(O)C>[CH2:24]([O:26][C:27]([C:28]1[CH:10]([C:9]2[CH:8]=[C:7]([O:12][CH3:13])[C:6]([O:14][CH3:15])=[CH:5][C:4]=2[N+:1]([O-:3])=[O:2])[C:17]2[C:16](=[O:23])[CH2:21][CH2:20][CH2:19][C:18]=2[NH:30][C:29]=1[NH2:31])=[O:32])[CH3:25]

Participants

5

Reactant 3

HCID 104341,3-CyclohexanedioneHCID 885056-NitroveratraldehydeHCID 4599837Carbamimidoyl-acetic acid ethyl ester

Product 1

HCID 70635419HCID 70635419, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Boiling a solution of 8.5 g of 6-nitroveratraldehyde, 4.0 g of cyclohexane-1,3-dione and 5.2 g of amidinoacetic acid ethyl ester in 150 ml of ethanol for 1 hour yields 2-amino-4-(2-nitro-4,5-dimethoxyphenyl)-1,4,5,6,7,8-hexahydro-5-oxoquinoline-3-carboxylic acid ethyl ester of melting point 261°C (ethanol).

Workup

  1. customfor 1 hour

Sources & evidence

ORD record
ord-d87c6629cd524435ba654ca0af3f8594
Source dataset
uspto-grants-1976_03
Patent number
US03946026

Reaction notes

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