Nitrogen → HCID 15228156, compound

HRID 863458Notes

Reaction equation

HRID 863458 reaction equation
[C:1]1([C:7]2[CH:8]=[N:9][C:10]3[N:11]=[CH:12][CH:13]=[C:14]([CH:17]=O)[C:15]=3[CH:16]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:19]/[C:20](/[CH3:24])=[CH:21]\[C:22]#[N:23].[C:25]([O:31][CH2:32][CH3:33])(=[O:30])[CH2:26][C:27]([CH3:29])=O.N#N>C(O)C>[C:22]([C:21]1[CH:17]([C:14]2[CH:13]=[CH:12][N:11]=[C:10]3[C:15]=2[CH:16]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:8]=[N:9]3)[C:26]([C:25]([O:31][CH2:32][CH3:33])=[O:30])=[C:27]([CH3:29])[NH:19][C:20]=1[CH3:24])#[N:23]

Participants

6

Reactant 4

HCID 947NitrogenHCID 8868Ethyl AcetoacetateHCID 5325263(2Z)-3-Amino-2-butenenitrileHCID 19696475HCID 19696475, compound

Product 1

HCID 15228156HCID 15228156, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2 g (8.54 mmol) of 3-phenyl-1,8-naphthyridine-5-carboxaldehyde, 0.7 g (8.54 mmol) of 3-aminocrotononitrile and 1.08 ml of ethyl acetoacetate (8.54 mmol) are boiled in 16 ml of ethanol in an N2 atmosphere for 16 hours. Chromatography over silica gel and elution with ethyl acetate gives 0.38 g (10.8% of theory) of the title compound of melting point 265° C.

Workup

  1. washChromatography over silica gel and elution with ethyl acetate

Sources & evidence

ORD record
ord-f0cbba4b0d3d44eb8cc6edb744860d6a
Source dataset
uspto-grants-1998_02
Patent number
US05721248

Reaction notes

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