Pyridine → 1-(3-Bromophenyl)-2-(diallylamino)ethanone oxime
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8](=O)[CH2:9][N:10]([CH2:14][CH:15]=[CH2:16])[CH2:11][CH:12]=[CH2:13])[CH:5]=[CH:6][CH:7]=1.N1C=CC=CC=1.Cl.[NH2:25][OH:26]>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:8](=[N:25][OH:26])[CH2:9][N:10]([CH2:14][CH:15]=[CH2:16])[CH2:11][CH:12]=[CH2:13])[CH:5]=[CH:6][CH:7]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
A solution of 1-(3-bromophenyl)-2-(diallylamino)ethanone (60 g, 204.7 mmol) in ethanol (720 mL) and pyridine (24.8 mL, 307 mmol) is stirred 15 minutes at 22° C. Hydroxylamine hydrochloride (17 g, 246 mmol) is added in portions to the solution over 1 hour. The reaction is warmed to 50° C. for 2 hours and then heated to 70° C. for 16 hours. The solvent is evaporated and the residue partitioned in water (300 mL) and methyl tert-butyl ether (300 mL). The organic layer is separated and washed with water (100 mL, 2×) and brine (100 mL). The organic layer is dried over sodium sulfate, filtered, and evaporated to dryness to give the title compound (75.5 g, 79%). ES/MS (m/e): 309 (M+1).
Workup
- temperatureheated to 70° C. for 16 hours
- customThe solvent is evaporated
- customthe residue partitioned in water (300 mL)
- customThe organic layer is separated
- washwashed with water (100 mL, 2×) and brine (100 mL)
- dry with materialThe organic layer is dried over sodium sulfate
- filtrationfiltered
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-16f1318051a84d1cb9a5ca68f45dd825
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08987254B2
Reaction notes
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