Sodium Hydroxide → 2-Chloro-3-[(methylsulfonyl)amino]benzoic acid
Reaction equation
[Cl:1][C:2]1[C:11]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].[OH-].[Na+]>>[Cl:1][C:2]1[C:11]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]Participants
3
Procedure
To a solution of methyl 3-amino-2-chlorobenzoate (517 mg, 2.79 mmol) and pyridine (0.25 mL, 3.06 mmol) in 8 mL CH2Cl2 was added methanesulfonylchloride (0.24 mL, 3.06 mmol). After washing with 1M HCl, methyl 2-chloro-3-[(methylsulfonyl)amino]benzoate was isolated as a solid in quantitative yield. 1H NMR (400 MHz, CDCl3), δ 7.77 (dd, 1H, J=8.2, 1.6 Hz), 7.61 (dd, 1H, J=7.9, 1.6 Hz), 7.33 (t, 1H, J=7.9 Hz), 7.16 (s, 1H), 3.91 (s, 3H), 2.99 (5, 3H); ESI-MS 262 (M−H). Methyl 2-chloro-3-[(methylsulfonyl)amino]benzoate was hydrolyzed using aqueous NaOH to provide 2-chloro-3-[(methylsulfonyl)amino]benzoic acid as a solid, which was used without further purification. ESI-MS 248 (M−H).
Sources & evidence
- ORD record
- ord-3ad3fa785aeb44ce87ac6d2e2ae6c4c3
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07645771B2
Reaction notes
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