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

HRID 333536Notes

Reaction equation

HRID 333536 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>[Pd].C(O)C>[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 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3-nitro-N-phenylpyridin-2-amine (29 g, 135 mmol) and palladium on carbon (10 wt %, 3 g) in ethanol (200 mL) were hydrogenated on a Parr hydrogenator at 45 psi for 8 h. The catalyst was filtered. The solution was concentrated to give N2-phenylpyridine-2,3-diamine (20 g, 80% yield).

Workup

  1. filtrationThe catalyst was filtered
  2. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-d0eb23e386224da1a9b9e883f05aaadf
Source dataset
uspto-grants-2014_11
Patent number
US08883322B2

Reaction notes

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