2-Amino-5-chloro-3-nitropyridine → 5-Chloropyridine-2,3-diamine

HRID 53592

Reaction equation

HRID 53592 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([Cl:11])=[CH:4][N:3]=1>[Ni].CO>[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([Cl:11])=[CH:4][N:3]=1

Participants

4

Reactant 1

HCID 2241682-Amino-5-chloro-3-nitropyridine

Product 1

HCID 12682545-Chloropyridine-2,3-diamineYield 96.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of the nitropyridine 2 (22.0 g 126.8 mmol), Raney Ni (2.2 g) and MeOH (220 mL) was shaken under H2 (20-40 psi) for 3 h, then filtered. The filtrate was rota-evaporated and the residual solid was dried to give 17.57 g (96%) of 3 as a tan powder, mp 169°-171° C. (lit. 172°-173° C, (Israel, M. & Day, A. R., J. Org. Chem. 24:1455-1460 (1959))). 1H NMR (DMSO-d6), 4.991 (bs, 2H), 5.555 (bs, 2H), 6.675 (d, 1H, J=2), 7.196 (d, 1H, J=2).

Workup

  1. filtrationfiltered
  2. customThe filtrate was rota-evaporated
  3. customthe residual solid was dried

Sources & evidence

ORD record
ord-b74b60a64491406d9bc03297253419b6
Source dataset
uspto-grants-1997_04
Patent number
US05620978

Linked notes

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