3-Hydroxybenzaldehyde → 3-((Methylamino)methyl)phenol

10.0 g of 3-hydroxybenzaldehyde and 9.55 g of a 40% methanol solution of methylamine were mixed, and then the solvent was evaporated. The resulting Schiff base was dissolved in 50 ml of ethanol, and with stirring under ice cooling, 10.0 g of sodium borohydride was added. The mixture was stirred overnight at room temperature. The solvent was evaporated under reduced pressure, and ethyl acetate and a saturated aqueous solution of sodium chloride were added to extract it. The organic layer was separated, and dried over anhydrous sodium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography Wakogel C-100, 100 g; eluting solvent: methylene chloride/methanol=10/1→5/1) to give 8.88 g (yield Λ%) of N-methyl-3-hydroxybenzylamine as pale yellow crystals, m.p. 138°-140° C.

1. customthe solvent was evaporated
2. dissolutionThe resulting Schiff base was dissolved in 50 ml of ethanol
3. addition10.0 g of sodium borohydride was added
4. stirringThe mixture was stirred overnight at room temperature
5. customThe solvent was evaporated under reduced pressure, and ethyl acetate
6. additiona saturated aqueous solution of sodium chloride were added
7. extractionto extract it
8. customThe organic layer was separated
9. dry with materialdried over anhydrous sodium sulfate
10. customThe solvent was evaporated
11. customthe residue was purified by silica gel column chromatography Wakogel C-100, 100 g

ORD record

ord-4a316b5964a249cfb951bf6bcfb326cc

Source dataset

uspto-grants-1993_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05234946