Sodium Hydroxide → 2-[2-(4-Fluoro-benzoylamino)-phenyl]-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid

HRID 1036908Notes

Reaction equation

HRID 1036908 reaction equation
[F:1][C:2]1[CH:33]=[CH:32][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH:15]2[CH2:24][C:23]([CH3:26])([CH3:25])[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([C:27]([O:29]CC)=[O:28])[CH:21]=3)[NH:16]2)=[O:7])=[CH:4][CH:3]=1.O.[OH-].[Li+].[OH-].[Na+]>C(O)C.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH:15]2[CH2:24][C:23]([CH3:26])([CH3:25])[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([C:27]([OH:29])=[O:28])[CH:21]=3)[NH:16]2)=[O:7])=[CH:32][CH:33]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 168937Lithium hydroxide, monohydrateHCID 67290770HCID 67290770, compound

Product 1

HCID 569669332-[2-(4-Fluoro-benzoylamino)-phenyl]-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of ethyl 2-(2-(4-fluorobenzamido)phenyl)-4,4-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate (about 0.62 mmol) in ethanol was added a solution of lithium hydroxide monohydrate (129 mg, 3.08 mmol) and sodium hydroxide (50 mg, 1.23 mmol) in water at room temperature. The reaction mixture was concentrated in vacuo. The residue was diluted with water, adjusted pH=3˜4 by 1M aqueous hydrochloric acid, extracted with ethyl acetate. The combined organic layer was washed by brine, dried over anhydrous sodium sulfate, concentrated in vacuo. The residue was purified by HPLC to give 2-[2-(4-fluoro-benzoylamino)-phenyl]-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid LC/MS m/e obsd. (ESI+) [(M+H)+] 419.10.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionThe residue was diluted with water
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layer was washed by brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-7dc45a4c62e34a4d9fa96369e8702fbd
Source dataset
uspto-grants-2013_10
Patent number
US08546427B2

Reaction notes

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