Methylamine → 2-Methoxy-5-[(methylamino)methyl]phenol

Methylamine (40% aqueous solution, 2.2 mL, 25 mmol) is added to a solution of 3-hydroxy-4-methoxybenzaldehyde (3.0 g, 20 mmol) in ethanol (35 mL). The resulting slurry is stirred for 30 minutes at room temperature. Then the solvents were evaporated under reduced pressure. The resulting solid is dissolved in methanol (300 mL) and sodium borohydride (0.90 g, 24 mmol) is added. The reaction mixture is stirred for 2 hours at room temperature and then concentrated under reduced pressure. The residue is partitioned between saturated aqueous potassium carbonate solution and ethyl acetate. The aqueous phase is extracted 3× with ethyl acetate, and the combined extracted were concentrated under reduced pressure to give 2-methoxy-5-methylaminomethyl-phenol as a granular white solid (2.5 g, 75%).

1. customThen the solvents were evaporated under reduced pressure
2. dissolutionThe resulting solid is dissolved in methanol (300 mL)
3. stirringThe reaction mixture is stirred for 2 hours at room temperature
4. concentrationconcentrated under reduced pressure
5. customThe residue is partitioned between saturated aqueous potassium carbonate solution and ethyl acetate
6. extractionThe aqueous phase is extracted 3× with ethyl acetate
7. extractionthe combined extracted
8. concentrationwere concentrated under reduced pressure

ORD record

ord-cad3046dac7742998d9af4d3c41014f0

Source dataset

uspto-grants-2010_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07713994B2