Hydroxyamine hydrochloride → 2-(5-Aminoisoxazol-3-yl)-2-methylpropanenitrile

HRID 538642Notes

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]=1

Participants

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
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08865744B1

Reaction notes

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