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

HRID 509647Notes

Reaction equation

HRID 509647 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-996bbfa716ca4ce1b163b10fbae208df
Source dataset
uspto-grants-2015_08
Patent number
US09096590B2

Reaction notes

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