Hydrochloric Acid → 4-Methoxy-3-(morpholine-4-sulfonyl)benzoic acid
Reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9]C)=[O:8])=[CH:5][C:4]=1[S:13]([N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)(=[O:15])=[O:14].[OH-].[Na+].Cl>CO>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[S:13]([N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)(=[O:14])=[O:15]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To methyl 4-methoxy-3-(morpholinosulfonyl)benzoate 41 (0.970 g, 3.08 mmol) was added NaOH (0.599 g, 15.0 mmol) (15 mL, 1 M in water) followed by methanol (10 mL). The reaction mixture was heated to 60° C. for 2 h and acidified with 1 M HCl. The organic phase was extracted with EtOAc (5×) and the combined extracts were washed with brine (1×), dried over MgSO4, filtered, and concentrated to yield 4-methoxy-3-(morpholinosulfonyl)benzoic acid 42 (0.824 g, 88.9% yield) as a white solid which was used without further purification. Mass spectrum: calculated for C12H15NO6S 301.1. found 302.1 (M++1).
Workup
- extractionThe organic phase was extracted with EtOAc (5×)
- washthe combined extracts were washed with brine (1×)
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-c204ae1acf61413995f1da24bfb991cb
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08349831B2
Reaction notes
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