Sodium Sulfite → Methyl 3-amino-4-chloro-2-[(2-hydroxyethyl)amino]benzoate
Reaction equation
[NH2:1][C:2]1[C:3]([NH:12][CH2:13][CH2:14][OH:15])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[Cl:16]N1C(=O)CCC1=O.S([O-])([O-])=O.[Na+].[Na+]>ClCCl>[NH2:1][C:2]1[C:3]([NH:12][CH2:13][CH2:14][OH:15])=[C:4]([CH:9]=[CH:10][C:11]=1[Cl:16])[C:5]([O:7][CH3:8])=[O:6]Participants
5
Conditions
- Temperature
- 30 °C
Procedure
To a solution of methyl 3-amino-2-[(2-hydroxyethyl)amino]benzoate (114.1 mg, 0.543 mmol) in dichloromethane (2.7 mL) was added N-chlorosuccinimide (14.5 mg, 1.09 mmol) at room temperature. The mixture was stirred at room temperature for 1.5 hr and at 30° C. for 0.5 hr. Aqueous sodium sulfite was added to the reaction mixture at room temperature and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with a 25-70% ethyl acetate/n-hexane gradient mixture to give the title compound (29.0 mg, 0.12 mmol, 22%) as an orange amorphous.
Workup
- extractionthe mixture was extracted with ethyl acetate
- washThe organic layer was washed with water and brine
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated in vacuo
- customThe residue was purified by flash chromatography on silica gel eluting with a 25-70% ethyl acetate/n-hexane gradient mixture
Sources & evidence
- ORD record
- ord-a0939b1476fe44aab265823d02591e53
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08785460B2
Reaction notes
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