Hydrochloric Acid → 2-Methoxy-4-methylbenzenemethanamine

Temperature

60 °C

To a solution of 2-methoxy-4-methylbenzamide (14.55 g, 88.08 mmol) in dry THF (50 mL) was added dropwise Borane-tetrahydrofuran complex (1.0 M in THF, 220 mL, 2.5 eq) at 0° C. under N2 atmosphere. The reaction mixture was then heated to 60° C. overnight. The reaction was cooled to room temperature, aq.HCl (6 N, 37 mL) was added carefully and the reaction mixture was then heated at 70° C. for 2 hrs. After cooling, water was added and the resulting solution was washed with ether. The aqueous layer was basified with aq. NaOH (10 N) at 0° C. and saturated with K2CO3 then extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, filtered and evaporated to give 8.5 g of (2-methoxy-4-methylphenyl)methanamine. (64% yield)

1. temperatureThe reaction was cooled to room temperature
2. temperaturethe reaction mixture was then heated at 70° C. for 2 hrs
3. temperatureAfter cooling
4. washthe resulting solution was washed with ether
5. customwas basified with aq. NaOH (10 N) at 0° C. and saturated with K2CO3
6. extractionthen extracted with ethyl acetate
7. washThe organic layer was washed with brine
8. dry with materialdried over MgSO4
9. filtrationfiltered
10. customevaporated

ORD record

ord-82aa13881ab941199ee5d7c53a4935b0

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08318947B2