4-Amino-1-methyl-3-nitro-1,8-naphthyridin-2(1H)-one → 3,4-Diamino-1-methyl-1,8-naphthyridin-2(1H)-one

HRID 1376223Notes

Reaction equation

HRID 1376223 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]([CH3:12])[C:4](=[O:13])[C:3]=1[N+:14]([O-])=O>[Pd].CCO.C1COCC1>[NH2:14][C:3]1[C:4](=[O:13])[N:5]([CH3:12])[C:6]2[C:11]([C:2]=1[NH2:1])=[CH:10][CH:9]=[CH:8][N:7]=2

Participants

4

Reactant 1

HCID 451232974-Amino-1-methyl-3-nitro-1,8-naphthyridin-2(1H)-one

Product 1

HCID 451232963,4-Diamino-1-methyl-1,8-naphthyridin-2(1H)-oneYield 94.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

A solution of 4-amino-1-methyl-3-nitro-1H-[1,8]naphthyridin-2-one (1.35 g, 6.13 mmol) in 1:1 EtOH/THF (25 mL) was hydrogenated over 10% Pd/C (1.30 g, 1.23 mmol) at room temperature. After 2 h, the catalyst was removed by filtration, rinsing with MeOH. The filtrate was concentrated to provide 3,4-diamino-1-methyl-1H-[1,8]naphthyridin-2-one (1.10 g, 94% yield). 1H-NMR (DMSO): δ 8.39 (dd, 1H, J=4.8, 1.6 Hz), 8.19 (dd, 1H, J=6.4, 1.6 Hz), 7.24 (dd, 1H, J=8.0, 4.8 Hz), 5.58 (s, 2H), 4.52 (s, 2H), 3.69 (s, 3H). MS: calculated for C9H10N4O+H 191.1; found: 191.2.

Workup

  1. customthe catalyst was removed by filtration
  2. washrinsing with MeOH
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-97b4b04b85054155bff9c2d936383488
Source dataset
uspto-grants-2007_01
Patent number
US07169926B1

Reaction notes

Loading…