4-amino-1-benzyl-3-nitro-1H-pyridin-2-one → 3,4-diamino-1-benzyl-1H-pyridin-2-one

HRID 1376211Notes

Reaction equation

HRID 1376211 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:4](=[O:15])[C:3]=1[N+:16]([O-])=O>[Pd].CCO.C1COCC1>[NH2:16][C:3]1[C:4](=[O:15])[N:5]([CH2:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:6]=[CH:7][C:2]=1[NH2:1]

Participants

4

Reactant 1

HCID 219476414-amino-1-benzyl-3-nitro-1H-pyridin-2-one

Product 1

HCID 219476293,4-diamino-1-benzyl-1H-pyridin-2-oneYield 93.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

A solution of 4-amino-1-benzyl-3-nitro-1H-pyridin-2-one (1.10 g, 4.49 mmol) in 1:3 EtOH/THF (20 mL) was hydrogenated over 10% Pd/C (0.48 g, 0.45 mmol) at room temperature. After 1 h, the catalyst was removed by filtration, rinsing with MeOH. The filtrate was concentrated to provide 3,4-diamino-1-benzyl-1H-pyridin-2-one (0.90 g, 93% yield). 1H-NMR (DMSO): δ 7.32 (m, 2H), 7.23 (m, 3H), 6.98 (d, 1H, J=7.6 Hz), 5.80 (d, 1H, J=7.2 Hz), 5.22 (m, 2H), 5.0 (s, 2H), 4.11 (m, 2H). MS: calculated for C12H13N3O+H 216.1; found: 216.1.

Workup

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

Sources & evidence

ORD record
ord-f928d4b255a04559a466faf02d2cc356
Source dataset
uspto-grants-2007_01
Patent number
US07169926B1

Reaction notes

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