4-chloro-2-[(methylamino)methyl]phenol synthesis
- Product Name:4-chloro-2-[(methylamino)methyl]phenol
- CAS Number:38926-77-1
- Molecular formula:C8H10ClNO
- Molecular Weight:171.62
Yield:38926-77-1 88%
Reaction Conditions:
Stage #1: 5-chlorosalicyclaldehyde;methylamine in methanol;water at 2; for 2 h;
Stage #2: with sodium tetrahydroborate;water in methanol at 0 - 20;
Steps:
a) 4-Chloro-2-((methylamino)methyl)phenol
5-Chloro-2-hydroxybenzaldehyde (1.00 g, 6.39 mmol) was dissolved in methanol (69 mL). Under anhydrous atmosphere, methanamine (40% in water, 11 mL, 126.00 mmol) was added and the reaction was stirred at room temperature for 2 hours. Then the reaction mixture was cooled to 0°C and sodium borohydride (0.48 g, 12.70 mmol) was added and stirred at room temperature overnight. The crude was evaporated under reduced pressure and purified directly by flash chromatography (dichloromethane to dichloromethane/methanol/ammonia (80:20:2)) to yield the title compound (1.04 g, 88%) as a white solid.LRMS (mz): 172, 174 (M÷1, M÷3).
References:
WO2017/220431,2017,A1 Location in patent:Page/Page column 44; 45
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