Pyridine → 3-(Methylsulfonamido)benzoic Acid
Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7]C)=[O:6].N1C=CC=CC=1.[CH3:18][S:19](Cl)(=[O:21])=[O:20].[OH-].[Na+]>ClCCl.CO.O>[CH3:18][S:19]([NH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([OH:7])=[O:6])(=[O:21])=[O:20]Participants
Procedure
To a solution of methyl 3-amino-benzoate (2.0 g, 13.2 mmol) and pyridine (2.30 g, 29.1 mmol) in dichloromethane (50 ml) at −10° C. under a nitrogen atmosphere was slowly added methanesulfonyl chloride (2.25 ml, 29.1 mmol) by syringe. After 2 hours, water was added and the volatiles were removed by spin evaporation in vacuo. A solution of the residue and sodium hydroxide (3.175 g, 79.4 mmol) in methanol (50 ml) and water (50 ml) was stirred for 18 hours. The residue after removal of the volatiles by spin evaporation in vacuo was dissolved in 1 N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water and the volatiles were removed by spin evaporation in vacuo to give 3-[(methylsulfonyl)amino]benzoic acid as an oil. (1.32 g, 46%). 1H-NMR (400 MHz, DMSO-d6): δ 7.83-7.78 (m, 2H), 7.55-7.50 (m, 1H), 7.50-7.46 (m, 1H), 3×80 (s, 3H). ES-LCMS m/z 216 (M+H).
Workup
- customat −10° C.
- customthe volatiles were removed by spin evaporation in vacuo
- customThe residue after removal of the volatiles
- customby spin evaporation in vacuo
- dissolutionwas dissolved in 1 N hydrochloric acid
- extractionextracted with ethyl acetate
- washThe organic layer was washed with water
- customthe volatiles were removed by spin evaporation in vacuo
Sources & evidence
- ORD record
- ord-f90ce1c935b94835b9b8fe89232c4861
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07645771B2
Reaction notes
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