Dimethylformamide dimethyl acetal → 1,5-dimethyl-1,6-naphthyridin-2(1H)-one

HRID 462719Notes

Reaction equation

HRID 462719 reaction equation
[CH3:1][C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6](=[O:12])[NH:7]2.[CH3:13]OC(OC)N(C)C>CN(C)C=O>[CH3:13][N:7]1[C:8]2[C:3](=[C:2]([CH3:1])[N:11]=[CH:10][CH:9]=2)[CH:4]=[CH:5][C:6]1=[O:12]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 5362132Medorinone

Product 1

HCID 132320511,5-dimethyl-1,6-naphthyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

E-9. 1,5-Dimethyl-1,6-naphthyridin-2(1H)-one--A mixture containing 4.5 g of 5-methyl-1,6-naphthyridin-2(1H)-one, 15 ml of dimethylformamide and 4 ml of dimethylformamide dimethyl acetal was stirred at room temperature overnight, then heated on a steam bath for 7 hours and then evaporated to dryness on a rotary evaporator. The solid residue was recrystallized from isopropyl alcohol and dried at 90°-95° C. to yield 3.5 g of 1,5-dimethyl-1,6-naphthyridin-2(1H)-one, m.p. 203°-205° C.

Workup

  1. temperatureheated on a steam bath for 7 hours
  2. customevaporated to dryness on a rotary evaporator
  3. customThe solid residue was recrystallized from isopropyl alcohol
  4. customdried at 90°-95° C.

Sources & evidence

ORD record
ord-d5bde7a471ac4592b320109a5ef7aa8a
Source dataset
uspto-grants-1985_05
Patent number
US04517190

Reaction notes

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