Bromine → 2-Amino-5-bromopyridine-3-carbonitrile
Reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[Br:10]Br>C(O)C>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([Br:10])=[CH:6][C:7]=1[C:8]#[N:9]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of commercially available 2-amino-3-cyanopyridine (15 g, 126 mmol) in ethanol (250 mL) at 0° C. was dropwise added bromine (6.7 mL, 130 mmol) and the mixture was stirred at 0° C. for 2 h, then at 23° C. for 16 h. The solvent was totally evaporated, water (200 mL) was added, then sat. NaHCO3-solution until neutral. Extracted with AcOEt (3×300 mL), the organic layer was dried over Na2SO4, filtered and totally evaporated. The residue was triturated with ether to give the title compound as a light yellow solid (23.5 g, 94%). MS (ISP) 198.1 [(M+H)+], 200.2 [(M+2+H)+].
Workup
- customat 0° C.
- waitat 23° C. for 16 h
- customThe solvent was totally evaporated
- additionwater (200 mL) was added
- extractionExtracted with AcOEt (3×300 mL)
- dry with materialthe organic layer was dried over Na2SO4
- filtrationfiltered
- customtotally evaporated
- customThe residue was triturated with ether
Sources & evidence
- ORD record
- ord-c0b1b7c264c14d7188fbb9348ce50d80
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08063048B2
Reaction notes
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