Acetyl bromide → 4-Bromo-1-oxo-2-(pyridin-2-yl)-1lambda~5~-pyridine

HRID 395232Notes

Reaction equation

HRID 395232 reaction equation
[N+]([C:4]1[CH:5]=[C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[N+:7]([O-:10])=[CH:8][CH:9]=1)([O-])=O.C([Br:20])(=O)C>C(O)(=O)C>[Br:20][C:4]1[CH:5]=[C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[N+:7]([O-:10])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 10482Acetyl bromideHCID 33312824-Nitro-2,2'-bipyridine-N-oxide

Product 1

HCID 181727784-Bromo-1-oxo-2-(pyridin-2-yl)-1lambda~5~-pyridineYield 95%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 4-nitro-2,2′-bipyridyl-N-oxide (Wenkert, D.; Woodward, R. B. J. Org. chem. 48, 283(1983)) (5 g) dissolved in 30 mL acetic acid in a 100 ml round bottom flask was added 16 mL acetyl bromide. The yellow mixture was refluxed for 1.5 h and then rotovaporated to dryness. The resulting light yellow solid was sufficiently pure enough for the next step without further purification. Yield: 95%

Workup

  1. temperatureThe yellow mixture was refluxed for 1.5 h
  2. customThe resulting light yellow solid was sufficiently pure enough for the next step without further purification

Sources & evidence

ORD record
ord-ca00a58ae7184af2a2f09dc9646072de
Source dataset
uspto-grants-2003_08
Patent number
US06605200B1

Reaction notes

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