5,7-diethyl-[1,6]naphthyridin-2(1H)-one → 5,7-diethyl-3,4-dihydro-1,6-naphthyridin-2(1H)-one

HRID 1492306Notes

Reaction equation

HRID 1492306 reaction equation
[CH2:1]([C:3]1[N:12]=[C:11]([CH2:13][CH3:14])[CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][C:7](=[O:15])[NH:8]2)[CH3:2]>C(O)C.[Pd]>[CH2:1]([C:3]1[N:12]=[C:11]([CH2:13][CH3:14])[CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][C:7](=[O:15])[NH:8]2)[CH3:2]

Participants

4

Reactant 1

HCID 200942525,7-diethyl-[1,6]naphthyridin-2(1H)-one

Product 1

HCID 200942545,7-diethyl-3,4-dihydro-1,6-naphthyridin-2(1H)-oneYield 95.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 5,7-diethyl-1,6-naphthyridin-2(1H)-one (10.0 g) in ethanol (100 ml) was catalytically hydrogenated over 10% palladium on carbon (1 g) at 50° C. and a pressure of 20 atmospheres for 30 hours. The catalyst was removed by filtration through diatomaceous earth and the filtrate was concentrated under vacuum to give 5,7-diethyl-1,2,3,4-tetrahydro-1,6-naphthyridin-2-one (9.6 g), m.p. 90°-94° C.; NMR: 1.2-1.3(m, 6H), 2.6-2.85(m, 6H), 3.05(t, 2H), 6.5(s, 1H), 8.9(br s, 1H).

Workup

  1. customThe catalyst was removed by filtration through diatomaceous earth
  2. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-c4141a68b21241f19068dd00c4d7af42
Source dataset
uspto-grants-1994_12
Patent number
US05373015

Reaction notes

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