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

HRID 517461Notes

Reaction equation

HRID 517461 reaction equation
CC[OH:3].[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 EtOH (150 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 for 14 h at ambient temperature. The catalyst was removed by filtration. The clear filtrate was evaporated to provide the crude product. The crude was subjected to column chromatography (60-120 silica gel, 30% ethyl acetate in hexane) to provide the title compound as a light yellow solid [1.1 g, 23%]. 1H NMR (300 MHz, DMSO-d6): δ 7.89 (brs, 1H), 7.79 (d, J=1.8 Hz, 1H), 7.40 (brs, 1H), 7.38 (d, J=1.8 Hz, 1H), 7.04 (brs, 2H): LC-MS (ESI): Calculated mass: 215.0; Observed mass: 216.8 [M+H]+ (RT: 0.38 min).

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-533caeb756234c218ef1d89e52c04c0a
Source dataset
uspto-grants-2015_08
Patent number
US09115092B2

Reaction notes

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