Dimethyl Sulfoxide → (S)-2-(2-nitrophenylamino)propan-1-ol
Reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].CS(C)=O.C(=O)([O-])[O-].[K+].[K+].[NH2:21][C@@H:22]([CH3:25])[CH2:23][OH:24]>O>[N+:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:21][C@@H:22]([CH3:25])[CH2:23][OH:24])([O-:10])=[O:9]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
A 200-mL round bottomed flask equipped with a magnetic stir bar was charged with 1-fluoro-2-nitrobenzene (8.25 g, 58.5 mmol), DMSO (29 mL), potassium carbonate (8.89 g, 64.3 mmol), and (S)-2-aminopropane-1-ol (4.83 g, 64.3 mmol). The mixture was heated to 60° C. for 6 h and then cooled to room temperature. The reaction mixture was diluted with water (60 mL). The mixture was stirred for several minutes, then extracted with ethyl acetate (ca. 200-250 mL). The ethyl acetate extract was washed thrice with 5 wt % aqueous sodium chloride (3×50 mL) and concentrated under reduced pressure to afford crude (S)-2-(2-nitrophenylamino)propane-1-ol (12.0 g, 105%) as a bright orange syrup. MS (ESI, pos. ion) m/z 197 [M+1]+.
Workup
- customA 200-mL round bottomed flask equipped with a magnetic stir bar
- temperaturecooled to room temperature
- extractionextracted with ethyl acetate (ca. 200-250 mL)
- extractionThe ethyl acetate extract
- washwas washed thrice with 5 wt % aqueous sodium chloride (3×50 mL)
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-f06376066ed64bf7bc6ecb1e5c4d7dc4
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09422281B2
Reaction notes
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