Hydroxyamine hydrochloride → HCID 53860723, compound
Reaction equation
Cl.[NH2:2][OH:3].C[O-].[Na+].[Na].[Br:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]#[N:17])=[C:11]([F:18])[CH:10]=1>CO>[OH:3][N:2]=[C:16]([NH2:17])[CH2:15][C:12]1[CH:13]=[CH:14][C:9]([Br:8])=[CH:10][C:11]=1[F:18]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Hydroxylamine hydrochloride (8.93 g, 128.5 mmol), was added in one portion to a solution of sodium methoxide, freshly prepared from sodium (2.96 g, 128.5 mmol) in methanol (200 mL). The resulting mixture was stirred 1 hour at room temperature, during which a precipitate was formed. 4-Bromo-2-fluorophenylacetonitrile (11.0 g, 51.4 mmol) was added and the resulting mixture heated to reflux for 20 hours. A white solid was removed by filtration of the hot mixture and discarded. The filtrate was concentrated to a volume of 100 mL to give a precipitate which was washed with water, followed by 5% EtOAc/hexanes. A second crop was obtained from the filtrate upon further concentration. The two crops were combined and dried in vacuo to give the product as a white crystalline solid (10.4 g, 82%) of sufficient purity for use in the subsequent reaction.
Workup
- customwas formed
- temperaturethe resulting mixture heated
- temperatureto reflux for 20 hours
- customA white solid was removed by filtration of the hot mixture
- concentrationThe filtrate was concentrated to a volume of 100 mL
- customto give a precipitate which
- washwas washed with water
- customA second crop was obtained from the filtrate upon further concentration
- customdried in vacuo
Sources & evidence
- ORD record
- ord-9df4cdd2d4674943b50a15718790ce91
- Source dataset
- uspto-grants-1990_01
- Patent number
- US04895862
Reaction notes
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