6-Chloro-2-nitropyridin-3-amine → 6-Chloropyridine-2,3-diamine

HRID 2199902Notes

Reaction equation

HRID 2199902 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([N+:8]([O-])=O)[C:5]([NH2:11])=[CH:4][CH:3]=1>[Ni].CO>[Cl:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([NH2:11])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 190227926-Chloro-2-nitropyridin-3-amine

Product 1

HCID 106306156-Chloropyridine-2,3-diamineYield 95.6%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of 6-chloro-2-nitropyridin-3-amine (E-23) (8.8 g, 51 mmol, 1.0 eq) and Raney nickel (0.88 g) in Methanol (100 mL) was stirred under hydrogen at RT for 24 h, then filtered and the filtrate was concentrated in vacuo to afford the desired product 6-chloropyridine-2,3-diamine (E-24) (7 g, 95.6% yield) as a pale solid. ESI-MS m/z: 144.05[M+H]+.

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-39e65342d8764118be4671ec8605e277
Source dataset
uspto-grants-2016_06
Patent number
US09359352B2

Reaction notes

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