Ammonia → 2-Amino-3-cyclopropyl-2-methyl-propionitrile

To a solution of 1-cyclopropyl-propan-2-one (CAN 4160-75-2; 1.0 g, 10.2 mmol) and aqueous ammonia (25% in water, 10 mL) in ethanol (10 mL) was added ammonium chloride (1.63 g, 30.6 mmol). The reaction mixture was stirred at ambient temperature for 1 hour. To this was added potassium cyanide (1 g, 15.30 mmol) portion wise, and the reaction mixture was stirred at ambient temperature for 12 h. Ice water (50 mL) was added and extracted with ethyl acetate (3×50 mL). The organic phases were washed with ice-water, combined, dried with Na2SO4 and concentrated in vacuo to give the title compound (0.8 g, 62.99%) as yellow oil; NMR (400 MHz, DMSO) δ=2.52 (bds, 2H); 1.6-1.5 (m, 1H); 1.49-1.4 (m, 1H); 1.39 (S, 3H); 0.85-0.75 (m, 1H); 0.49-0.44 (m, 2H); 0.16-0.14 (m, 2H).

1. stirringthe reaction mixture was stirred at ambient temperature for 12 h
2. extractionextracted with ethyl acetate (3×50 mL)
3. washThe organic phases were washed with ice-water
4. dry with materialdried with Na2SO4
5. concentrationconcentrated in vacuo

ORD record

ord-9a122a45d1c7443ea2b1ad9668b0ced7

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09321727B2