N-methyl-2-pyrrolidone → 6-Amino-4-chloro-3-pyridinecarbonitrile

Temperature

135 °C

(Tsuruoka, A., et. al. ibid) Zinc cyanide (0.254 g, 2.17 mmol) and tetrakistriphenylphosphine palladium (0) (0.460 g, 0.394 mmol) were added to a solution of compound ii (1.00 g, 3.94 mmol) in NMP (10 mL). The reaction mixture was heated under N2(g) to 135° C. for 2 h, cooled to room temperature and partitioned between EtOAc (30 mL) and aqueous ammonia solution (0.35%, 50 mL). The organic fraction was separated, washed successively with water (2×100 mL) and brine (30 mL), dried (MgSO4) and reduced in vacuo onto SiO2. Column chromatography (SiO2), eluting with 2:1 Petrol-EtOAc to 1:1 Petrol-EtOAc, afforded compound iii. (0.360 g, 2.35 mmol, 60%) as an off-white solid.

1. temperaturecooled to room temperature
2. custompartitioned between EtOAc (30 mL) and aqueous ammonia solution (0.35%, 50 mL)
3. customThe organic fraction was separated
4. washwashed successively with water (2×100 mL) and brine (30 mL)
5. dry with materialdried (MgSO4)
6. washColumn chromatography (SiO2), eluting with 2:1 Petrol-EtOAc to 1:1 Petrol-EtOAc

ORD record

ord-54073b5151ff488caf7bde80a234b311

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09060515B2