Formamidine acetate → Medorinone

HRID 1649169Notes

Reaction equation

HRID 1649169 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7](=[O:15])[NH:8][C:9]=1[CH:10]=[CH:11][N:12](C)C)(=O)[CH3:2].C(O)(=O)C.C(N)=N>CN(C)C=O>[CH3:2][C:1]1[N:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][C:7](=[O:15])[NH:8]2

Participants

4

Reactant 2

HCID 160693Formamidine acetateHCID 37350622(1H)-Pyridinone, 5-acetyl-6-[2-(dimethylamino)ethenyl]-

Product 1

HCID 5362132MedorinoneYield 83.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture containing 10.3 g of 5-acetyl-6-(2-dimethylaminoethenyl)-2(1H)-pyridinone, 10.4 g of formamidine acetate and 75 ml of dimethylformamide was heated on a steam bath for 5 hours and then concentrated to dryness on a rotary evaporator. The residue was treated with 50 ml of water and again stripped to dryness. The white residue was recrystallized from isopropyl alcohol to yield 6.7 g of 5-methyl-1,6naphthyridin-2(1H)-one, m.p. 238°-240° C. This compound was the same as the compound of Example E-7a, e.g., a mixed melting point showed no depression and the infrared and nuclear magnetic resonance spectral data for the compounds were respectively the same.

Workup

  1. temperaturewas heated on a steam bath for 5 hours
  2. concentrationconcentrated to dryness on a rotary evaporator
  3. additionThe residue was treated with 50 ml of water
  4. customThe white residue was recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-741331532e4c478ca0afa91472238baa
Source dataset
uspto-grants-1983_11
Patent number
US04415580

Reaction notes

Loading…