Sodium Hydroxide → 2-(4-Chloro-3-(cyclohexanecarboxamido)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid

HRID 1801315Notes

Reaction equation

HRID 1801315 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:17]([CH3:19])([CH3:18])[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:20]([O:22]C)=[O:21])[CH:14]=3)[NH:9]2)=[CH:4][C:3]=1[NH:24][C:25]([CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1)=[O:26].[OH-].[Na+]>CO.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:17]([CH3:18])([CH3:19])[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:20]([OH:22])=[O:21])[CH:14]=3)[NH:9]2)=[CH:4][C:3]=1[NH:24][C:25]([CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1)=[O:26]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67442025Methyl 2-(4-chloro-3-(cyclohexanecarboxamido)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate

Product 1

HCID 584762182-(4-Chloro-3-(cyclohexanecarboxamido)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acidYield 14%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 2-(4-chloro-3-(cyclohexanecarboxamido)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate (380 mg, 0.835 mmol) in methanol (15 mL) was added a solution of sodium hydroxide (270 mg, 6.68 mmol) in water (6.8 mL). The mixture was stirred and heated to reflux for 5 h. The mixture was evaporated, and the residue was dissolved in 15 mL of water. The aqueous solution was acidified to pH=3 with 1M hydrochloric acid. The precipitated solid was collected by filtration, and dissolved in ethyl acetate. The organic layer was dried over sodium sulfate. After evaporation, the mixture was purified on silica gel to afford 50 mg of 2-(4-chloro-3-(cyclohexanecarboxamido)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid as an off white solid. (Yield: 14%) MS (ESI+APCI) M+1=423.2, M−1=441.0.

Workup

  1. temperatureheated
  2. temperatureto reflux for 5 h
  3. customThe mixture was evaporated
  4. dissolutionthe residue was dissolved in 15 mL of water
  5. filtrationThe precipitated solid was collected by filtration
  6. dissolutiondissolved in ethyl acetate
  7. dry with materialThe organic layer was dried over sodium sulfate
  8. customAfter evaporation
  9. customthe mixture was purified on silica gel

Sources & evidence

ORD record
ord-a56e45259d104ef2b34d8e2a5d40996e
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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