4-Amino-1,2-dihydropyridin-2-one → 3-Acetyl-2-methyl-4-[4-nitro-2-(trifluoromethyl)phenyl]-4,6-dihydro-1,6-naphthyridin-5(1H)-one

HRID 1951388Notes

Reaction equation

HRID 1951388 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][C:7]([CH:8]=[C:9]([C:13](=[O:15])[CH3:14])[C:10](=O)[CH3:11])=[C:6]([C:18]([F:21])([F:20])[F:19])[CH:5]=1)([O-:3])=[O:2].[NH2:22][C:23]1[CH:28]=[CH:27][NH:26][C:25](=[O:29])[CH:24]=1>C(O)(C)C>[C:13]([C:9]1[CH:8]([C:7]2[CH:16]=[CH:17][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]=2[C:18]([F:19])([F:20])[F:21])[C:24]2[C:25](=[O:29])[NH:26][CH:27]=[CH:28][C:23]=2[NH:22][C:10]=1[CH3:11])(=[O:15])[CH3:14]

Participants

4

Reactant 2

HCID 5735304-Amino-1,2-dihydropyridin-2-oneHCID 596030233-[4-Nitro-2-(trifluoromethyl)benzylidene]pentane-2,4-dione

Product 1

HCID 596030333-Acetyl-2-methyl-4-[4-nitro-2-(trifluoromethyl)phenyl]-4,6-dihydro-1,6-naphthyridin-5(1H)-one

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

1.28 g (4.24 mmol) of 3-[4-nitro-2-(trifluoromethyl)benzylidene]pentane-2,4-dione and 484 mg (4.24 mmol) of 4-aminopyridin-2(1H)-one [Searls, T., McLaughlin, L. W., Tetrahedron 55, 11985-11996 (1999)] are dissolved in 25 ml of isopropanol and heated under reflux under argon for 12 h. Cooling is followed by filtration, and the remaining solid is washed with diethyl ether (40 ml). 990 mg (58% of theory) of the title compound are obtained as a white solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux under argon for 12 h
  3. temperatureCooling
  4. filtrationis followed by filtration
  5. washthe remaining solid is washed with diethyl ether (40 ml)

Sources & evidence

ORD record
ord-7f9f1533215c4828930e23cbdfe42c8d
Source dataset
uspto-grants-2013_03
Patent number
US08404709B2

Reaction notes

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