Sodium Hydroxide → HCID 67441800, compound

HRID 1801389Notes

Reaction equation

HRID 1801389 reaction equation
[CH3:1][C:2]1([CH3:32])[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:12]([O:14]C)=[O:13])[CH:9]=2)[NH:4][CH:3]1[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([S:22](=[O:31])(=[O:30])[NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:17]=1.[OH-].[Na+]>CO.O1CCCC1>[CH3:1][C:2]1([CH3:32])[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:12]([OH:14])=[O:13])[CH:9]=2)[NH:4][CH:3]1[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([S:22](=[O:31])(=[O:30])[NH:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:17]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67440469HCID 67440469, compound

Product 1

HCID 67441800HCID 67441800, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 3,3-dimethyl-2-(3-(N-phenylsulfamoyl)phenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylate (130 mg, 0.29 mmol) in methanol/tetrahydrofuran (5 mL/5 mL) was added 1N sodium hydroxide (4.33 mL). The resultant mixture was heated to reflux for 2.5 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 dissolved in tetrahydrofuran, dried over anhydrous magnesium sulfate. anhydrous magnesium sulfate was removed, and after evaporation, the residue was purified on preparative Thin layer chromatography to afford 80 mg of crude product, which was recrystallized from dichloromethane and ether to afford 40 mg of 3,3-dimethyl-2-(3-(N-phenylsulfamoyl)phenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylic acid. (Yield: 32%). MS (ESI+APCI) M+1=437.1.

Workup

  1. temperatureto reflux for 2.5 h
  2. customOrganic solvent was removed
  3. dissolutionthe residue was dissolved in water
  4. filtrationThe precipitates were filtered
  5. dissolutiondissolved in tetrahydrofuran
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customanhydrous magnesium sulfate was removed
  8. customafter evaporation
  9. customthe residue was purified on preparative Thin layer chromatography
  10. customto afford 80 mg of crude product, which
  11. customwas recrystallized from dichloromethane and ether

Sources & evidence

ORD record
ord-bfcb8f6f2cf9445585423dde408eb4a6
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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