2-chloro-5-nitropyridin-4-amine → 6-Chloropyridine-3,4-diamine

HRID 2409047

Reaction equation

HRID 2409047 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH2:8])[C:5]([N+:9]([O-])=O)=[CH:4][N:3]=1>CCOC(C)=O.[Ni]>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([NH2:9])=[C:6]([NH2:8])[CH:7]=1

Participants

4

Reactant 1

HCID 109100582-chloro-5-nitropyridin-4-amine

Product 1

HCID 8171336-Chloropyridine-3,4-diamineYield 107.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-chloro-5-nitropyridin-4-amine (4.50 g, 25.93 mmol) in EtOAc (100 mL) was added Raney nickel (0.45 g) followed by stirring under hydrogen at RT for 2 h. The reaction mixture was filtered and the filtrate concentrated under reduced pressure to afford 4.00 g (ca. 100%) of crude 6-chloropyridine-3,4-diamine as yellow oil. MS (ESI): m/z=144.3 [M+1]+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-6be8b6661d27469f9649a4b31d83a784
Source dataset
uspto-grants-2014_08
Patent number
US08815877B2

Linked notes

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