Hydroxyamine hydrochloride → 2-(5-Aminoisoxazol-3-yl)-2-methylpropanenitrile
Reaction equation
[NH2:1][C:2]([C:6]([CH3:10])([CH3:9])[C:7]#[N:8])=[CH:3][C:4]#[N:5].N[OH:12].Cl>CO>[NH2:5][C:4]1[O:12][N:1]=[C:2]([C:6]([CH3:10])([CH3:9])[C:7]#[N:8])[CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
To 3-Amino-4,4-dimethyl-pent-2-endinitrile (10.0 g, 74 mmol) in MeOH (150 mL) is added NH2OH.HCl (10.0 g, 144 mmol). The mixture is stirred at 40° C. for 7 h, concentrated, suspended in isopropyl acetate (100 mL) and washed with 4 N aq. NaOH (2×100 mL) and brine (50 mL). The extracted org. layer is concentrated to provide 7.40 g of 2-(5-Amino-isoxazol-3-yl)-2-methyl-propionitrile. Yield: 66%; ESI-MS: 152 [M+H]+; 1H-NMR (DMSO-d6): 1.6, 5.1, 6.8 ppm.
Workup
- concentrationconcentrated
- washwashed with 4 N aq. NaOH (2×100 mL) and brine (50 mL)
- concentrationlayer is concentrated
Sources & evidence
- ORD record
- ord-517464bbbc3547638e27e1d2fb2d05a7
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08865744B1
Reaction notes
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