Ethanol → 2-Ethylamino-3-nitropyridine

HRID 333549Notes

Reaction equation

HRID 333549 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:11]([NH2:13])[CH3:12].C(O)C>>[CH2:11]([NH:13][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1)[CH3:12]

Participants

4

Reactant 3

HCID 702EthanolHCID 6341EthylamineHCID 796132-Chloro-3-nitropyridine

Product 1

HCID 120157272-Ethylamino-3-nitropyridineYield 92%

Procedure

2-Chloro-3-nitropyridine (20.00 g, 126 mmol) was added to ethylamine in ethanol (40 mL, 80 mmol) at room temperature and kept overnight. The solution was evaporated, the residue was diluted with 150 mL of EtOAc, washed with aqueous NaHCO3 and purified by column chromatography on silica gel (hexane/ethyl acetate 4/1) to give yellow solid (19.5 g, 92%).

Workup

  1. customThe solution was evaporated
  2. additionthe residue was diluted with 150 mL of EtOAc
  3. washwashed with aqueous NaHCO3
  4. custompurified by column chromatography on silica gel (hexane/ethyl acetate 4/1)

Sources & evidence

ORD record
ord-73ac23f5c8694659b3474991d37be063
Source dataset
uspto-grants-2014_11
Patent number
US08883322B2

Reaction notes

Loading…