5,7-diethyl-1-(4-nitrobenzyl)-1,6-naphthyridin-2(1H)-one → 1-(4-aminobenzyl)-5,7-diethyl-1,6-naphthyridin-2(1H)-one

HRID 1492311Notes

Reaction equation

HRID 1492311 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:25])[N:8]2[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=1)[CH3:2]>C1COCC1.[Pt](=O)=O>[NH2:22][C:19]1[CH:18]=[CH:17][C:16]([CH2:15][N:8]2[C:9]3[C:4](=[C:3]([CH2:1][CH3:2])[N:12]=[C:11]([CH2:13][CH3:14])[CH:10]=3)[CH:5]=[CH:6][C:7]2=[O:25])=[CH:21][CH:20]=1

Participants

4

Reactant 1

HCID 189523915,7-diethyl-1-(4-nitrobenzyl)-1,6-naphthyridin-2(1H)-one

Product 1

HCID 189523881-(4-aminobenzyl)-5,7-diethyl-1,6-naphthyridin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of compound B (16.0 g) in THF (200 ml) was cataltically hydrogenated over platinum (IV) oxide (320 mg) at one atmosphere for 3 hours. The catalyst was removed by filtration and the solvent was removed by evaporation to give 1-(4-aminobenzyl)-5,7-diethyl-1,6-naphthyridin-2(1H)-one (C) as an off white solid (14.5 g), m.p. 164°-165° C.; NMR (d6 -DMSO): 1.85(t, 3H), 1.2(t, 3H), 2.72(q, 2H), 3.03(q, 2H), 5.1(s, 2H), 5.28(s, 2H), 6.48(d, 2H), 6.66(d, 1H), 6.94(d, 2H), 7.14(s, 1H), 8.16(d, 1H); mass spectrum (+ve FAB, MeOH/DMSO/NBA): 308 (M+H)+ ; microanalysis, found: C, 74.0; H, 6.9; N, 13.1%; C19H21N3O requires C, 74.2; H, 6.9; N, 13.1 %.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-c15c81fc65e24b65838bd815beb8dc14
Source dataset
uspto-grants-1994_12
Patent number
US05373015

Reaction notes

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