Monobasic potassium phosphate → 2-Methoxyisonicotinonitrile

Temperature

0 °C

A stirred suspension of 17.86 g NaOMe (330.7 mmol, 1.22 eq) in 95 mL acetonitrile was cooled to 0° C. and a solution of 37.56 g 2-chloro-4-cyano pyridine (8, 271.1 mmol) in 225 mL acetonitrile was added over 45 min. Stirring was continued at room temperature for 23 h until less than 4% (area) starting material were detected by HPLC. 11.1 g potassium dihydrogen phosphate (81.56 mmol, 0.30 eq) were added at 0° C. and stirring was continued for 3 h at room temperature. The reaction mixture was then evaporated to dryness in a rotary evaporator (40° C./10 mbar) yielding the crude product (64.94 g, 179% by weight) as a brown solid. 64.94 g crude product were extracted with 900 mL toluene for 18 h at reflux temperature using a soxhlet extraction apparatus yielding the title product (25.65 g, 71% by weight) as an orange solid.

1. stirringstirring
2. waitwas continued for 3 h at room temperature
3. customThe reaction mixture was then evaporated to dryness in a rotary evaporator (40° C./10 mbar)
4. customyielding the crude product (64.94 g, 179% by weight) as a brown solid
5. extraction64.94 g crude product were extracted with 900 mL toluene for 18 h
6. temperatureat reflux temperature
7. extractiona soxhlet extraction apparatus

ORD record

ord-8479e84f7f8f4fd89a840c6b2121f8aa

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07705155B2