5-Chloro-6-methyl-3-nitropyridin-2-amine → 5-Chloro-6-methylpyridine-2,3-diamine

HRID 53598Notes

Reaction equation

HRID 53598 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([Cl:11])=[C:4]([CH3:12])[N:3]=1>[Pd].CO>[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([Cl:11])=[C:4]([CH3:12])[N:3]=1

Participants

4

Reactant 1

HCID 122510135-Chloro-6-methyl-3-nitropyridin-2-amine

Product 1

HCID 249029185-Chloro-6-methylpyridine-2,3-diamineYield 88.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of the nitropyridine 46 (1.48 g, 7.85 mmol), MeOH (50 mL), and 5% Pd-C (150 mg) was shaken under H2 (20-30 psi) for 20 h. The mixture was filtered and the filtrate was rota-evaporated to dryness to give 1.09 g (87%) of the diamine 47 as a brown powder, mp 128°-130° C. 1H NMR (CDCl3) δ1.661 (s, 3H), 3.233 (bs, 2H), 4.183 (bs, 2H), 6.880 (s, 1H).

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was rota-evaporated to dryness

Sources & evidence

ORD record
ord-732409bfa79c4b7f8eb9b219e5ae5a05
Source dataset
uspto-grants-1997_04
Patent number
US05620978

Reaction notes

Loading…