Bromine → 2-(Acetylaminomethyl)-6-bromoacetylpyridine hydrobromide

HRID 1491815Notes

Reaction equation

HRID 1491815 reaction equation
[Br:1]Br.[C:3]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][NH:13][C:14](=[O:16])[CH3:15])[N:7]=1)(=[O:5])[CH3:4].[BrH:17].C(O)(=O)C>C(O)(=O)C.CO>[BrH:1].[C:14]([NH:13][CH2:12][C:8]1[CH:9]=[CH:10][CH:11]=[C:6]([C:3](=[O:5])[CH2:4][Br:17])[N:7]=1)(=[O:16])[CH3:15]

Participants

6

Reactant 3

HCID 24408BromineHCID 103753152-Acetyl-6-(acetylaminomethyl)pyridineHCID 21893785Acetic Acid Mixture with Hydrobromic Acid

Product 1

HCID 189538712-(Acetylaminomethyl)-6-bromoacetylpyridine hydrobromide

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 887MethanolSolvent

Procedure

A solution of bromine (1.56 g) in acetic acid (5 ml) was added dropwise to a solution of 2-acetyl-6-(acetylaminomethyl)pyridine (1.87 g) and 30 weight % hydrogen bromide-acetic acid solution (4.2 ml) in a mixture of acetic acid (40 ml) and methanol (10 ml) at ambient temperature with stirring. The mixture was warmed to 60° to 70° C. and stirred for two hours. The solvent was evaporated in vacuo and the residue was triturated with diisopropyl ether to give 2-(acetylaminomethyl)-6-bromoacetylpyridine hydrobromide (3.78 g). IR (Nujol) : 1720, 1620 cm-1 NMR (CD3OD, δ): 2.10 (3H, s), 3.90 (2H, s), 4.83 (2H, s), 7.77 (1H, br s), 8.13 (2H, t, J=8 Hz) and 8.70 (1H, t, J=8 Hz)

Workup

  1. temperatureThe mixture was warmed to 60° to 70° C.
  2. stirringstirred for two hours
  3. customThe solvent was evaporated in vacuo
  4. customthe residue was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-68195fd4f4704a72b489969f8b56c116
Source dataset
uspto-grants-1994_12
Patent number
US05371097

Reaction notes

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