N-benzyl-N-methyl-3-nitropyridin-2-amine → 2-N-methylpyridine-2,3-diamine

HRID 82583Notes

Reaction equation

HRID 82583 reaction equation
[CH2:1]([N:8](C)[C:9]1[C:14]([N+:15]([O-])=O)=[CH:13][CH:12]=[CH:11][N:10]=1)C1C=CC=CC=1>CCO.[Pd]>[CH3:1][NH:8][C:9]1[C:14]([NH2:15])=[CH:13][CH:12]=[CH:11][N:10]=1

Participants

4

Reactant 1

HCID 9211491N-benzyl-N-methyl-3-nitropyridin-2-amine

Product 1

HCID 123436692-N-methylpyridine-2,3-diamineYield 92.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of N-benzyl-N-methyl-3-nitropyridin-2-amine (15 g) and 10% Pd—C (6.56 g) in EtOH (300 mL) was hydrogenated under balloon pressure at room temperature over weekend. The catalyst was removed by filtration and the filtrate was concentrated in vacuo to give N2-methylpyridine-2,3-diamine (7.00 g) as a tan solid.

Workup

  1. waitwas hydrogenated under balloon pressure at room temperature over weekend
  2. customThe catalyst was removed by filtration
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-5101b913b3e247cca4f69c2fa01188fe
Source dataset
uspto-grants-2014_09
Patent number
US08846713B2

Reaction notes

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