Ethanol → 2-Ethylamino-3-nitropyridine

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

Reactant 3

HCID 702Ethanol

HCID 6341Ethylamine

HCID 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

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

Sources & evidence

ORD record: ord-73ac23f5c8694659b3474991d37be063
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883322B2

Reaction notes

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