3-Nitro-5-(trifluoromethyl)pyridin-2-amine → 5-(Trifluoromethyl)pyridine-2,3-diamine

HRID 53600Notes

Reaction equation

HRID 53600 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([C:11]([F:14])([F:13])[F:12])=[CH:4][N:3]=1>[Ni].CO>[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([C:11]([F:13])([F:12])[F:14])=[CH:4][N:3]=1

Participants

4

Reactant 1

HCID 106083913-Nitro-5-(trifluoromethyl)pyridin-2-amine

Product 1

HCID 102144255-(Trifluoromethyl)pyridine-2,3-diamineYield 100%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of 50 (950 mg, 4.59 mmol), methanol (15 mL) and Raney Ni (about 200 mg) was shaken under H2 (30-40 psi) for 2 h, then filtered. The filtrate was evaporated to dryness, giving 810 mg (100%) of the diamine 51 as a deep yellow powder, mp 97°-99° C. 1H NMR (CDCl3), 3.389 (bs, 2H), 4.556 (bs, 2H), 7.049 (s, 1H), 7.932 (s, 1H).

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-1295f323d1e344dfafda530c129efc63
Source dataset
uspto-grants-1997_04
Patent number
US05620978

Reaction notes

Loading…