Sodium Hydroxide → HCID 53492322, compound

HRID 1801365Notes

Reaction equation

HRID 1801365 reaction equation
[CH:1]([NH:4][S:5]([C:8]1[CH:9]=[C:10]([CH:14]2[C:23]([CH3:25])([CH3:24])[CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[C:19]([C:26]([O:28]C)=[O:27])[CH:20]=3)[NH:15]2)[CH:11]=[CH:12][CH:13]=1)(=[O:7])=[O:6])([CH3:3])[CH3:2].[OH-].[Na+]>CO.O1CCCC1>[CH:1]([NH:4][S:5]([C:8]1[CH:9]=[C:10]([CH:14]2[C:23]([CH3:24])([CH3:25])[CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[C:19]([C:26]([OH:28])=[O:27])[CH:20]=3)[NH:15]2)[CH:11]=[CH:12][CH:13]=1)(=[O:6])=[O:7])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67442053HCID 67442053, compound

Product 1

HCID 53492322HCID 53492322, compoundYield 28.5%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 2-(3-(N-isopropylsulfamoyl)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate (120 mg, 0.288 mmol) in methanol/tetrahydrofuran (4 mL/4 mL) was added 1N sodium hydroxide (4.32 mL). The resultant mixture was heated to reflux for 1.5 h. Organic solvent was removed and the residue was dissolved in water. The aqueous layer was acidified to pH=4. The precipitates were filtered, and redissolved in tetrahydrofuran, dried over anhydrous magnesium sulfate. anhydrous magnesium sulfate was removed, and after evaporation, the residue was treated with dichloromethane to afford 33 mg of 2-(3-(N-isopropylsulfamoyl)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid (Yield: 28%). MS (ESI+APCI) M+1=403.1.

Workup

  1. temperatureto reflux for 1.5 h
  2. customOrganic solvent was removed
  3. dissolutionthe residue was dissolved in water
  4. filtrationThe precipitates were filtered
  5. dissolutionredissolved in tetrahydrofuran
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customanhydrous magnesium sulfate was removed
  8. customafter evaporation
  9. additionthe residue was treated with dichloromethane

Sources & evidence

ORD record
ord-e6d633ffb06e415f8e8674b61717045b
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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