1-Naphthaldehyde → HCID 12391112, compound

HRID 918497Notes

Reaction equation

HRID 918497 reaction equation
[C:1]1([CH:11]=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:13]1(=[O:20])[CH2:18][CH2:17][CH2:16][C:15](=O)[CH2:14]1.[CH2:21]([O:23][C:24](=[O:29])[CH2:25][C:26](=[NH:28])[NH2:27])[CH3:22].C(O)C.CN(C=O)C>C(O)C>[CH2:21]([O:23][C:24]([C:25]1[CH:11]([C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)[C:14]2[C:13](=[O:20])[CH2:18][CH2:17][CH2:16][C:15]=2[NH:27][C:26]=1[NH2:28])=[O:29])[CH3:22]

Participants

6

Reactant 4

HCID 61951-NaphthaldehydeHCID 104341,3-CyclohexanedioneHCID 4599837Carbamimidoyl-acetic acid ethyl esterHCID 19794673N,N-dimethylformamide ethanol

Product 1

HCID 12391112HCID 12391112, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Upon boiling a solution of 6.3 g of 1naphthaldehyde, 4.5 g of cyclohexane-1,3-dione and 5.2 g of amidinoacetic acid ethyl ester in 150 ml of ethanol for 2 hours, 2-amino-4-(naphth-1-yl)-1,4,5,6,7,8-hexahydro-5-oxoquinoline-3-carboxylic acid ethyl ester of melting point 279°C (ethanol/DMF) is obtained. Yield: 64% of theory.

Workup

  1. customfor 2 hours

Sources & evidence

ORD record
ord-14f63c7cc18d45bab865f9520ef94b4b
Source dataset
uspto-grants-1976_07
Patent number
US03971791

Reaction notes

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