Hydrochloric Acid → Acetamide, N-[[6-(bromoacetyl)-2-pyridinyl]methyl]-
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].Cl.C(OC(C)C)(C)C>O1CCOCC1>[C:14]([NH:13][CH2:12][C:8]1[CH:9]=[CH:10][CH:11]=[C:6]([C:3](=[O:5])[CH2:4][Br:1])[N:7]=1)(=[O:16])[CH3:15]Participants
Procedure
Bromine (9.9 ml) was added dropwise to a mixture of 2-acetyl-6-(acetylaminometyl)pyridine (37.0 g) in dioxane (740 ml) and 4N-dioxanic hydrogen chloride (48.1 ml) at ambient temperature with stirring. After the mixture was stirred at 50° C. for 3 hours. To the mixture was added a diisopropyl ether (600 ml) and the mixture was stirred under ice-cooling for 30 minutes. The isolated precipitate was collected by filtration. The precipitate was added to water and the mixture was adjusted to pH 8 with 20% aqueous potassium carbonate. The aqueous mixture was extracted with a mixture of ethyl acetate and tetrahydrofuran. The extract was dried over magnesium sulfate and evaporated in vacuo to give 2-(acetylaminomethyl)-6-bromoacetylpyridine (50.3 g) as an oil. lR (Film): 1710, 1650 cm-1NMR (CDCl3 δ): 2.11 (3H, s), 4.63 (2H, d, J=5.3 Hz), 4.80 (2H, s), 7.43-7.59 (1H, m), 7.78-8.08 (2H, m)
Workup
- stirringAfter the mixture was stirred at 50° C. for 3 hours
- stirringthe mixture was stirred under ice-
- temperaturecooling for 30 minutes
- filtrationThe isolated precipitate was collected by filtration
- additionThe precipitate was added to water
- extractionThe aqueous mixture was extracted with a mixture of ethyl acetate and tetrahydrofuran
- dry with materialThe extract was dried over magnesium sulfate
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-6bda4d11b3914a79b09742f62fa119ee
- Source dataset
- uspto-grants-1994_11
- Patent number
- US05364871
Reaction notes
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