Potassium Carbonate → N-[6-(2-Bromoacetyl)-2-pyridinyl]acetamide

HRID 2379814Notes

Reaction equation

HRID 2379814 reaction equation
[Br:1]Br.[C:3]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH:12][C:13](=[O:15])[CH3:14])[N:7]=1)(=[O:5])[CH3:4].Br.C(O)(=O)C.C(=O)([O-])[O-].[K+].[K+]>C(O)(=O)C.O.C(OCC)(=O)C>[C:13]([NH:12][C:8]1[CH:9]=[CH:10][CH:11]=[C:6]([C:3](=[O:5])[CH2:4][Br:1])[N:7]=1)(=[O:15])[CH3:14]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 24408BromineHCID 10241363HCID 10241363, compoundHCID 21893785Acetic Acid Mixture with Hydrobromic Acid

Product 1

HCID 10106483N-[6-(2-Bromoacetyl)-2-pyridinyl]acetamide

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Bromine (1.9 ml) was added dropwise to a mixture of 2-acetyl-6-acetylaminopyridine (6.6 g) and 30 wt % hydrogenbromide-acetic acid solution (7.4 ml) in acetic acid (66 ml) at ambient temperature under stirring and the mixture was stirred at 50° C. for 1.5 hours. The reaction mixture was added to a mixture of ethyl acetate and water and the mixture was adjusted to pH 8 with potassium carbonate. The separated organic layer was washed with brine, dried over magnesium sulfate and evaporated to give 2-acetylamino-6-bromoacetylpyridine (8.57 g).

Workup

  1. stirringthe mixture was stirred at 50° C. for 1.5 hours
  2. washThe separated organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-7abee1dab207485383bc7aaa3e1620f3
Source dataset
uspto-grants-1994_11
Patent number
US05364871

Reaction notes

Loading…