Acetaldehyde → 2-Amino-4-methyl-1,4,5,6,7,8-hexahydro-5-oxoquinoline-3-carboxylic acid ethyl ester

HRID 268063Notes

Reaction equation

HRID 268063 reaction equation
[CH:1](=O)[CH3:2].[C:4]1(=[O:11])[CH2:9][CH2:8][CH2:7][C:6](=O)[CH2:5]1.[CH2:12]([O:14][C:15](=[O:20])[CH2:16][C:17](=[NH:19])[NH2:18])[CH3:13]>C(O)C>[CH2:12]([O:14][C:15]([C:16]1[CH:1]([CH3:2])[C:5]2[C:4](=[O:11])[CH2:9][CH2:8][CH2:7][C:6]=2[NH:19][C:17]=1[NH2:18])=[O:20])[CH3:13]

Participants

5

Reactant 3

HCID 177AcetaldehydeHCID 104341,3-CyclohexanedioneHCID 4599837Carbamimidoyl-acetic acid ethyl ester

Product 1

HCID 123911062-Amino-4-methyl-1,4,5,6,7,8-hexahydro-5-oxoquinoline-3-carboxylic acid ethyl esterYield 53%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Upon boiling a solution of 2.8 g of acetaldehyde, 5.6 g of cyclohexane-1,3-dione and 6.5 g of amidinoacetic acid ethyl ester in 100 ml of ethanol for 2 hours, 2-amino-4-methyl-1,4,5,6,7,8-hexahydro-5-oxoquinoline-3carboxylic acid ethyl ester of melting point 236°C (ethanol) is obtained.

Workup

  1. customfor 2 hours

Sources & evidence

ORD record
ord-b03513af0d3e48e5a28f9c9ea827990d
Source dataset
uspto-grants-1976_03
Patent number
US03946026

Reaction notes

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