2-Acetylnaphthalene → 4-(4-Nitrophenoxy)-7-oxo-7,8-dihydro[1,8]naphthyridine

HRID 1010183Notes

Reaction equation

HRID 1010183 reaction equation
[NH2:1][C:2]1[C:7](/[CH:8]=[CH:9]/[C:10](OCC)=[O:11])=[C:6]([O:15][C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=2)[CH:5]=[CH:4][N:3]=1.C(C1C=CC2C(=CC=CC=2)C=1)(=O)C>CO>[N+:22]([C:19]1[CH:20]=[CH:21][C:16]([O:15][C:6]2[C:7]3[CH:8]=[CH:9][C:10](=[O:11])[NH:1][C:2]=3[N:3]=[CH:4][CH:5]=2)=[CH:17][CH:18]=1)([O-:24])=[O:23]

Participants

4

Reactant 2

HCID 71222-AcetylnaphthaleneHCID 58931221Ethyl(E)-3-[2-amino-4-(4-nitrophenoxy)-3-pyridyl]-2-propenoate

Product 1

HCID 229368804-(4-Nitrophenoxy)-7-oxo-7,8-dihydro[1,8]naphthyridineYield 51.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl (E)-3-[2-amino-4-(4-nitrophenoxy)-3-pyridyl]-2-propenoate (350 mg), 2′-acetonaphthone (50 mg) and methanol (80 ml) were irradiated for 4 hours while stirring, and the precipitated solid was filtered out to obtain 156 mg of a light yellow solid.

Workup

  1. filtrationthe precipitated solid was filtered out

Sources & evidence

ORD record
ord-17dc2cb46c464552a75cd0f5b33f4431
Source dataset
uspto-grants-2011_07
Patent number
US07973160B2

Reaction notes

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