Sodium Hydroxide → 2-(3-Benzamido-5-chloro phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid

HRID 1801330Notes

Reaction equation

HRID 1801330 reaction equation
[C:1]([NH:9][C:10]1[CH:11]=[C:12]([CH:17]2[C:26]([CH3:28])([CH3:27])[CH2:25][C:24]3[C:19](=[CH:20][CH:21]=[C:22]([C:29]([O:31]C)=[O:30])[CH:23]=3)[NH:18]2)[CH:13]=[C:14]([Cl:16])[CH:15]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[C:1]([NH:9][C:10]1[CH:11]=[C:12]([CH:17]2[C:26]([CH3:28])([CH3:27])[CH2:25][C:24]3[C:19](=[CH:20][CH:21]=[C:22]([C:29]([OH:31])=[O:30])[CH:23]=3)[NH:18]2)[CH:13]=[C:14]([Cl:16])[CH:15]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67440903HCID 67440903, compound

Product 1

HCID 674407562-(3-Benzamido-5-chloro phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acidYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 2-(3-benzamido-5-chlorophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate (61 mg, 0.14 mmol) in methanol (4 mL) was added a 1 M solution of sodium hydroxide (1.63 mL, 1.63 mmol). The mixture was stirred and heated to reflux for 3 h. The mixture was concentrated, dissolved in water and acidified to pH=5-6. The precipitated solid was collected by filtration, dissolved in tetrahydrofuran, and dried over anhydrous magnesium sulfate. After evaporation of the organic solvent, the residue was purified by column chromatography (silica gel, petroleum ether:ethyl acetate=3:1) to afford 54 mg of 2-(3-benzamido-5-chloro phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid as a white solid. Yield: 91%; MS (ESI+APCI) M+1=417.

Workup

  1. temperatureheated
  2. temperatureto reflux for 3 h
  3. concentrationThe mixture was concentrated
  4. dissolutiondissolved in water
  5. filtrationThe precipitated solid was collected by filtration
  6. dissolutiondissolved in tetrahydrofuran
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customAfter evaporation of the organic solvent
  9. customthe residue was purified by column chromatography (silica gel, petroleum ether:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-a35b070ec10746498c7589e006374c47
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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