Hydrochloric Acid → 3-(Aminomethyl)phenol hydrochloride

Methanol (100 mL) and 10% palladium on carbon (2 g) were charged to a 250 mL Parr bottle followed by 3-cyanophenol (19.0 g, 0.1595 mol) and concentrated HCl (16.66 mL, 0.2 mol). The mixture was hydrogenated at room temperature and 50 psi until the uptake of hydrogen stopped (about 10 h). The reaction was filtered through a bed of Celite and the filter cake was washed with methanol (3×25 mL). The combined filtrates were evaporated under reduced pressure. Remaining volatiles were removed by evaporating the residue twice from 50 mL portions of absolute ethanol. The crude amine hydrochloride, essentially free of residual HCl, was dissolved with warming in a minimum amount of absolute ethanol (˜80 mL) and the stirred solution was diluted with anhydrous diethyl ether (500 mL). The mixture was stirred in an ice bath for 1 h then the colorless crystalline product was filtered off, washed with anhydrous diethyl ether (3×50 mL) and dried in vacuo to furnish (3-hydroxyphenyl)methylamine hydrochloride salt (20.6 g, 80.9%), mp 146-148° C.

1. customwas hydrogenated at room temperature
2. custom(about 10 h)
3. filtrationThe reaction was filtered through a bed of Celite
4. washthe filter cake was washed with methanol (3×25 mL)
5. customThe combined filtrates were evaporated under reduced pressure
6. customRemaining volatiles were removed
7. customby evaporating the residue twice from 50 mL portions of absolute ethanol
8. dissolutionThe crude amine hydrochloride, essentially free of residual HCl, was dissolved
9. temperaturewith warming in a minimum amount of absolute ethanol (˜80 mL)
10. additionthe stirred solution was diluted with anhydrous diethyl ether (500 mL)
11. filtrationthe colorless crystalline product was filtered off
12. washwashed with anhydrous diethyl ether (3×50 mL)
13. customdried in vacuo

ORD record

ord-33064b678923427ca4a53177a74ab6aa

Source dataset

uspto-grants-2004_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06803384B2