5-Bromo-4,6-dimethyl-3-nitro-2-pyridinylamine → HCID 178433488, compound

HRID 1454584Notes

Reaction equation

HRID 1454584 reaction equation
[Br:1][C:2]1[C:3]([CH3:13])=[C:4]([N+:10]([O-:12])=[O:11])[C:5](N)=[N:6][C:7]=1[CH3:8].N([O-])=[O:15].[Na+]>FC(F)(F)C(O)=O.O>[Br:1][C:2]1[C:3]([CH3:13])=[C:4]([N+:10]([O-:12])=[O:11])[C:5]([OH:15])=[N:6][C:7]=1[CH3:8]

Participants

4

Reactant 2

HCID 36499475-Bromo-4,6-dimethyl-3-nitro-2-pyridinylamineHCID 23668193Sodium Nitrite

Product 1

HCID 178433488HCID 178433488, compound

Reagents, catalysts & solvents 1

HCID 22392675Trifluoroacetic acid waterSolvent

Procedure

To a solution of 5-bromo-4,6-dimethyl-3-nitro-2-pyridinylamine (Heitsch, H.; et al. Bioorg. Med. Chem. 1997, 5, 673, 2.0 g, 8.1 mmol) in trifluoroacetic acid/water (v/v, 2:1, 30 mL) was added sodium nitrite (1.1 g, 16 mmol) in small portions at room temperature, and then the reaction mixture was stirred overnight. The resulting precipitates were collected by filtration, washed with water, and dried under reduced pressure to give 2.2 g (quant.) of the title compound: 1H-NMR (CDCl3) δ 2.53 (3H, s), 2.38 (3H, s).

Workup

  1. customThe resulting precipitates
  2. filtrationwere collected by filtration
  3. washwashed with water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-f889cf59da8c4e9c9545745928874403
Source dataset
uspto-grants-2009_01
Patent number
US07479564B2

Reaction notes

Loading…