Sodium Hydroxide → HCID 67441420, compound

HRID 2045561Notes

Reaction equation

HRID 2045561 reaction equation
[F: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](=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1.[OH-].[Na+]>O1CCCC1.O>[F: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]([OH:22])=[O:21])[CH:14]=3)[NH:9]2)=[CH:4][C:3]=1[NH:24][C:25](=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67439889HCID 67439889, compound

Product 1

HCID 67441420HCID 67441420, compoundYield 42.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 2-(4-fluoro-3-(picolinamido)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate (84 mg, 0.19 mmol) and sodium hydroxide (62 mg, 1.55 mmol) in tetrahydrofuran (10 mL), water (2 mL) was heated to reflux for 20 h. LC-MS showed the reaction was complete. The solvent was removed in vacuo and the residue was acidified by 1 M hydrochloric acid solution to pH=5-6. The precipitated white solid was collected by filtration and dissolved in acetone, dried over anhydrous magnesium sulfate. Removal of the solvent in vacuo gave crude product, which was purified by recrystallization from dichloromethane/Hexane/tetrahydrofuran to afford 30 mg of 2-(4-fluoro-3-(picolinamido)-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid. Yield: 42.1%. MS(ES+APCI) M+1=420.1.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 20 h
  3. customThe solvent was removed in vacuo
  4. filtrationThe precipitated white solid was collected by filtration
  5. dissolutiondissolved in acetone
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customRemoval of the solvent in vacuo
  8. customgave crude product, which
  9. customwas purified by recrystallization from dichloromethane/Hexane/tetrahydrofuran

Sources & evidence

ORD record
ord-00deb280bf8e4ee59e216f791c7c92e6
Source dataset
uspto-grants-2013_11
Patent number
US08586747B2

Reaction notes

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