Methyl iodide → 2-[2-(Dimethylamino)phenyl]propanoic acid
Reaction equation
[CH3:1][N:2]([CH3:13])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]([OH:12])=[O:11].[CH:14]([N-]C(C)C)(C)C.[Li+].C([Li])CCC.C(NC(C)C)(C)C.CI>O1CCCC1.CCCCCC.O.C(OCC)(=O)C>[CH3:13][N:2]([CH3:1])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]([CH3:14])[C:10]([OH:12])=[O:11]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 20 °C
Procedure
A solution of 2-[2-dimethylaminophenyl]acetic acid (1.8 g) in dry tetrahydrofuran (10 cc) is added at 10° C. to a solution of lithium diisopropylamide (prepared by the action of a 1.6M solution (2.6 cc) of butyllithium in hexane on a solution of diisopropylamine (2.8 g) in dry tetrahydrofuran (30 cc) at 10° C.). The reaction mixture is stirred for 30 minutes at 20° C. and then for 30 minutes at 35° C. After cooling to 20° C., methyl iodide (0.63 cc) is added and the mixture is heated for 1 hour at 35° C. The mixture is cooled and diluted with water (20 cc) and ethyl acetate (100 cc). The aqueous phase is washed with ethyl acetate (100 cc), acidified to pH 5 with hydrochloric acid and extracted with ethyl acetate (2×100 cc). The organic phases are washed with water, dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa) to give (RS)-2-[2-dimethylaminophenyl]propionic acid in the form of a yellow oil.
Workup
- waitfor 30 minutes at 35° C
- temperatureAfter cooling to 20° C.
- temperaturethe mixture is heated for 1 hour at 35° C
- temperatureThe mixture is cooled
- washThe aqueous phase is washed with ethyl acetate (100 cc)
- extractionextracted with ethyl acetate (2×100 cc)
- washThe organic phases are washed with water
- dry with materialdried over magnesium sulphate
- concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
Sources & evidence
- ORD record
- ord-9a931a34a4a942df87d7ab5ee76a54c1
- Source dataset
- uspto-grants-1992_04
- Patent number
- US05102667
Reaction notes
Loading…