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 the residue was extracted with ethyl acetate and a saturated aqueous sodium chloride solution. 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→5/1to give 8.88 g (yield 79%) of N-methyl-3-hydroxybenzylamine as pale yellow crystals having a melting point of 138° to 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 The mixture
4. stirringwas stirred overnight at room temperature
5. customThe solvent was evaporated under reduced pressure
6. extractionthe residue was extracted with ethyl acetate
7. customThe organic layer was separated
8. dry with materialdried over anhydrous sodium sulfate
9. customThe solvent was evaporated
10. customthe residue was purified by silica gel column chromatography [Wakogel C-100, 100 g

ORD record

ord-3c77d12276624a95a622596495432ee5

Source dataset

uspto-grants-1993_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05234946