3-nitro-N-phenylpyridin-2-amine → 2-N-phenylpyridine-2,3-diamine

HRID 242797Notes

Reaction equation

HRID 242797 reaction equation
[N+:1]([C:4]1[C:5]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:6][CH:7]=[CH:8][CH:9]=1)([O-])=O>CCOC(C)=O.[Pd]>[C:11]1([NH:10][C:5]2[C:4]([NH2:1])=[CH:9][CH:8]=[CH:7][N:6]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 1

HCID 6117993-nitro-N-phenylpyridin-2-amine

Product 1

HCID 106790912-N-phenylpyridine-2,3-diamineYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (3-nitropyridin-2-yl)phenylamine (2.49 g, 0.0116 mol) and 10% Pd/C (40 mg) in EtOAc (100 mL) was degassed with a stream of nitrogen and then stirred at RT under a hydrogen atmosphere for 16 h. The suspension was then filtered through a pad of Celite® and then the filtrate was concentrated in vacuo affording N2-Phenylpyridine-2,3-diamine as a white solid (2.06 g, 96%). LCMS: RT 1.15 min [M+H]+ 186.0.

Workup

  1. customwas degassed with a stream of nitrogen
  2. filtrationThe suspension was then filtered through a pad of Celite®
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-75cfc5660dab40e5a48056fd32b138a7
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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