4-Amino-1,2-dihydropyridin-2-one → 4-(3-Acetyl-2-methyl-5-oxo-1,4,5,6-tetrahydro-1,6-naphthyridin-4-yl)-3-methoxybenzonitrile

HRID 1951376Notes

Reaction equation

HRID 1951376 reaction equation
[C:1]([C:4]([C:16](=[O:18])[CH3:17])=[CH:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][C:7]=1[O:14][CH3:15])(=O)[CH3:2].[NH2:19][C:20]1[CH:25]=[CH:24][NH:23][C:22](=[O:26])[CH:21]=1>C(O)(C)C>[C:16]([C:4]1[CH:5]([C:6]2[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][C:7]=2[O:14][CH3:15])[C:21]2[C:22](=[O:26])[NH:23][CH:24]=[CH:25][C:20]=2[NH:19][C:1]=1[CH3:2])(=[O:18])[CH3:17]

Participants

4

Reactant 2

HCID 5735304-Amino-1,2-dihydropyridin-2-oneHCID 591869164-(2-Acetyl-3-oxobut-1-en-1-yl)-3-methoxybenzonitrile

Product 1

HCID 596030154-(3-Acetyl-2-methyl-5-oxo-1,4,5,6-tetrahydro-1,6-naphthyridin-4-yl)-3-methoxybenzonitrile

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

18 g (74 mmol) of 4-(2-acetyl-3-oxobut-1-en-1-yl)-3-methoxybenzonitrile and 8.14 g (74 mmol) of 4-aminopyridin-2(1H)-one [Searls, T., McLaughlin, L. W., Tetrahedron 55, 11985-11996 (1999)] are dissolved in 40 ml of isopropanol and heated under reflux under argon for 4 days. The mixture is then concentrated and the residue is recrystallized from methanol. 18.1 g (70% of theory) of the title compound are obtained as a pale yellow solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux under argon for 4 days
  3. concentrationThe mixture is then concentrated
  4. customthe residue is recrystallized from methanol

Sources & evidence

ORD record
ord-df75074a140249c6808d63899529ea7b
Source dataset
uspto-grants-2013_03
Patent number
US08404709B2

Reaction notes

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