Methanol → HCID 15598836, compound

HRID 2292091Notes

Reaction equation

HRID 2292091 reaction equation
[CH3:1][CH:2]1[CH2:11][C:10](=[O:12])[NH:9][C:8]2[N:7]=[C:6](Br)[C:5]3[N:14]=[CH:15][CH:16]=[CH:17][C:4]=3[C:3]1=2.[C:18]([Cu])#[N:19].[C-]#N.[K+].CO>O>[CH3:1][CH:2]1[CH2:11][C:10](=[O:12])[NH:9][C:8]2[N:7]=[C:6]([C:18]#[N:19])[C:5]3[N:14]=[CH:15][CH:16]=[CH:17][C:4]=3[C:3]1=2

Participants

6

Reactant 4

HCID 887MethanolHCID 9032Potassium CyanideHCID 15598817HCID 15598817, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 15598836HCID 15598836, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2 g (0.007 mol) of 1-methyl-6-bromo-1,2-dihydropyrido[2,3-c][1,8]naphthyridin-3(4H)-one, 0.3 g (0.003 mol) of CuCN and 0.3 g (0.005 mol) of KCN are heated for 7 hours at 160° C. in an autoclave with 20 ml of methanol and 10 ml of water. After cooling, the mixture is filtered under suction, and the residue digested in chloroform/methanol, 1:1, under reflux for 4 hours. The organic phase is filtered, dried and concentrated. The residue is purified by recrystallization from ethanol/petroleum ether, and 0.5 g (60.1% of theory) of 1-methyl-6-cyano-1,2-dihydropyrido[2,3-c][1,8]naphthyridin-3(4H)-one is obtained.

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture is filtered under suction
  3. temperaturethe residue digested in chloroform/methanol, 1:1, under reflux for 4 hours
  4. filtrationThe organic phase is filtered
  5. customdried
  6. concentrationconcentrated
  7. customThe residue is purified by recrystallization from ethanol/petroleum ether

Sources & evidence

ORD record
ord-b7b424c19fc84060a576a719ceaa89fc
Source dataset
uspto-grants-1989_01
Patent number
US04801590

Reaction notes

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