4-Amino-1,2-dihydropyridin-2-one → 3-Acetyl-2-methyl-4-(2-methyl-4-oxo-4H-chromen-8-yl)-4,6-dihydro-1,6-naphthyridin-5(1H)-one

HRID 1951368Notes

Reaction equation

HRID 1951368 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[C:9]([C:10](=[O:12])[CH:11]=1)=[CH:8][CH:7]=[CH:6][C:5]=2[CH:13]=[C:14]([C:18](=[O:20])[CH3:19])[C:15](=O)[CH3:16].[NH2:21][C:22]1[CH:27]=[CH:26][NH:25][C:24](=[O:28])[CH:23]=1>C(O)(C)C>[C:18]([C:14]1[CH:13]([C:5]2[CH:6]=[CH:7][CH:8]=[C:9]3[C:4]=2[O:3][C:2]([CH3:1])=[CH:11][C:10]3=[O:12])[C:23]2[C:24](=[O:28])[NH:25][CH:26]=[CH:27][C:22]=2[NH:21][C:15]=1[CH3:16])(=[O:20])[CH3:19]

Participants

4

Reactant 2

HCID 5735304-Amino-1,2-dihydropyridin-2-oneHCID 591869153-[(2-Methyl-4-oxo-4H-chromen-8-yl)methylene]pentane-2,4-dione

Product 1

HCID 596030093-Acetyl-2-methyl-4-(2-methyl-4-oxo-4H-chromen-8-yl)-4,6-dihydro-1,6-naphthyridin-5(1H)-one

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

4.00 g (14.79 mmol) of 3-[(2-methyl-4-oxo-4H-chromen-8-yl)methylene]pentane-2,4-dione and 1.63 g (14.79 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 at the reflux temperature under argon for 4 days. The mixture is then concentrated and the residue is recrystallized from methanol. 4.1 g (76% of theory) of the title compound are obtained as a yellow solid.

Workup

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

Sources & evidence

ORD record
ord-67f74abdd66c40b6acd4b073b354a4c9
Source dataset
uspto-grants-2013_03
Patent number
US08404709B2

Reaction notes

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