HCID 15598817, compound → HCID 15598839, compound

HRID 2292094Notes

Reaction equation

HRID 2292094 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(O)C.C(O)(=O)C.[Pd]>[CH3:1][CH:2]1[CH2:11][C:10](=[O:12])[NH:9][C:8]2[N:7]=[CH:6][C:5]3[NH:14][CH2:15][CH2:16][CH2:17][C:4]=3[C:3]1=2

Participants

5

Reactant 1

HCID 15598817HCID 15598817, compound

Product 1

HCID 15598839HCID 15598839, compoundYield 64.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

1.5 g (0.005 mol) of 1-methyl-6-bromo-1,2-dihydropyrido[2,3-c][1,8]naphthyridin-3(4H)-one are hydrogenated for 24 hours at room temperature and atmospheric pressure in a mixture of 100 ml of ethanol and 100 ml of glacial acetic acid with Pd/C (0.3 g/10%) with addition of 0.4 g (0.005 mol) of Na-acetate. The catalyst is removed by filtration under suction, the filtrate is concentrated, and the residue is recrystallized from ethanol. 0.7 g (64.4% of theory) of 1-methyl-1,2,7,8,9,10-hexahydropyrido[2,3-c][1,8]naphthyridin-3(4H)one is obtained.

Workup

  1. customThe catalyst is removed by filtration under suction
  2. concentrationthe filtrate is concentrated
  3. customthe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-0ac0e7d6add24d04a98750466b77ef5d
Source dataset
uspto-grants-1989_01
Patent number
US04801590

Reaction notes

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