Water → (S)-2-(2-amino-4-bromophenylamino)propan-1-ol

Temperature

80 °C

A 2-L, three-necked, round bottomed flask fitted with a nitrogen inlet, overhead stirrer, thermocouple, and condenser was charged with iron power (117 g, 2090 mmol), ammonium chloride (1.118 g, 20.90 mmol), ethanol (375 mL), and water (201 mL). The mixture was heated to 80° C., and a solution of (S)-2-(4-bromo-2-nitrophenylamino)propane-1-ol (57.5 g, 209 mmol) in ethanol (200 mL) was slowly added. The mixture stirred at 80° C. for 4 h. The reaction mixture was filtered through a pad of Celite and washed with ethanol (100 mL). The filtrate was concentrated under reduced pressure to remove the ethanol, and the resulting aqueous slurry stirred at rt for 3 h. The slurry was then filtered, and the solids were washed with water (100 mL) and dried under a nitrogen atmosphere overnight to afford (S)-2-(2-amino-4-bromophenylamino)propane-1-ol (47.55 g, 89%) as an off-white solid. MS (ESI, pos. ion) m/z 245 [M+1]+.

1. filtrationThe reaction mixture was filtered through a pad of Celite
2. washwashed with ethanol (100 mL)
3. concentrationThe filtrate was concentrated under reduced pressure
4. customto remove the ethanol
5. stirringthe resulting aqueous slurry stirred at rt for 3 h
6. filtrationThe slurry was then filtered
7. washthe solids were washed with water (100 mL)
8. customdried under a nitrogen atmosphere overnight

ORD record

ord-6f6089f00e734947b4c3c104e54fd1f2

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09422281B2