Ethanol → 3-Amino-5-bromopyridine-2-carboxamide

HRID 2284399Notes

Reaction equation

HRID 2284399 reaction equation
C([OH:3])C.[Br:4][C:5]1[CH:6]=[C:7]([N+:13]([O-])=O)[C:8]([C:11]#[N:12])=[N:9][CH:10]=1.C(OCC)(=O)C>[Ni].CCCCCC>[NH2:13][C:7]1[C:8]([C:11]([NH2:12])=[O:3])=[N:9][CH:10]=[C:5]([Br:4])[CH:6]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 8857Ethyl AcetateHCID 27696985-Bromo-3-nitropyridine-2-carbonitrile

Product 1

HCID 210758623-Amino-5-bromopyridine-2-carboxamideYield 23%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8058HexaneSolvent

Procedure

To a 100 mL round bottom flask, Raney Nickel (2.5 g) and ethanol (15 mL) were added. To the same flask, was added 5-bromo-3-nitropyridine-2-carbonitrile (5 g, 0.0219 mol). The reaction mass was stirred under hydrogen atmosphere for 14 hours at ambient temperature. The catalyst was removed by filtration. The clear filtrate was evaporated to provide the crude product. The crude material was subject to column chromatography (60-120 silica gel, 30% ethyl acetate in hexane) to provide title compound as a light yellow solid (1.1 g, 23%). 1H NMR (300 MHz, DMSO-d6): δ 7.89 (br s, 1H), 7.79 (d, J=1.8 Hz, 1H), 7.40 (br s, 1H), 7.38 (d, J=1.8 Hz, 1H), 7.04 (br s, 2H).

Workup

  1. customThe catalyst was removed by filtration
  2. customThe clear filtrate was evaporated
  3. customto provide the crude product

Sources & evidence

ORD record
ord-d78e23fae19b47ef92faf44ee8baf93a
Source dataset
uspto-grants-2015_09
Patent number
US09145411B2

Reaction notes

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