2-Fluoro-3-methoxybenzaldehyde oxime → (2-Fluoro-3-methoxyphenyl)methanamine

To a stirred solution of the oxime (14) (1.50 g, 8.86 mmol) in ethanol (70 mL) under nitrogen was added 10% palladium on carbon (100 mg). The reaction mixture was placed under an atmosphere of hydrogen and stirred at RT for 2 hr. The reaction mixture was filtered through Celite™, and was then evaporated in vacuo to remove the ethanol. The resultant crude residue was partitioned between ethyl acetate (50 mL) and aq hydrochloric acid (2 M, 50 mL). The aq layer was separated and was neutralised with saturated sodium hydrogen carbonate solution and then re-extracted with ethyl acetate (70 mL) followed by a mixture of 2-propanol and chloroform (1:1, 2×70 mL). The propanol/chloroform extracts were dried, filtered and evaporated in vacuo separately to afford the title compound (15) in two batches (batch 1: 346 mg, 25%; batch 2: 370 mg, 27%) as white solids: m/z 156 (M+H)+ (ES+) (method C).

1. filtrationThe reaction mixture was filtered through Celite™
2. customwas then evaporated in vacuo
3. customto remove the ethanol
4. customThe resultant crude residue was partitioned between ethyl acetate (50 mL) and aq hydrochloric acid (2 M, 50 mL)
5. customThe aq layer was separated
6. extractionre-extracted with ethyl acetate (70 mL)
7. additionfollowed by a mixture of 2-propanol and chloroform (1:1, 2×70 mL)
8. dry with materialThe propanol/chloroform extracts were dried
9. filtrationfiltered
10. customevaporated in vacuo separately

ORD record

ord-cfc71dc0395b4ae9a842f5b8a8d3a440

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08741909B2