Hydroxylamine, sulfate (1:1) → 2-(5-Aminoisoxazol-3-yl)-2-methylpropanenitrile

Reaction equation

[CH3:1][C:2]([CH3:10])([C:5](=O)[CH2:6][C:7]#[N:8])[C:3]#[N:4].S(O)(O)(=O)=O.NO.C(C1C=C(N)[O:23][N:22]=1)(C)C>>[NH2:8][C:7]1[O:23][N:22]=[C:5]([C:2]([CH3:10])([CH3:1])[C:3]#[N:4])[CH:6]=1

Participants

Reactant 3

HCID 159255Hydroxylamine, sulfate (1:1)

HCID 21152083-(Propan-2-yl)-1,2-oxazol-5-amine

HCID 866201652,2-Dimethyl-3-oxopentanedinitrile

Product 1

HCID 668766082-(5-Aminoisoxazol-3-yl)-2-methylpropanenitrileYield 23%

Procedure

Prepared from 2,2-dimethyl-3-oxopentanedinitrile (500 mg, 3.68 mmol) and hydroxylamine sulfate (332 mg, 2.02 mmol) according to the method described for 3-isopropylisoxazol-5-amine in Example 122A Step 2. Purification via silica gel chromatography eluting with 5% to 60% ethyl acetate in hexanes, afforded 2-(5-aminoisoxazol-3-yl)-2-methylpropanenitrile as a colorless solid (130 mg, 23%). 1H NMR (300 MHz, CDCl3) δ 5.22 (s, 1H), 4.58 (brs, 2H), 1.72 (s, 6H); LC-MS (ESI) m/z 152 (M+H)+.