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

HRID 1801295Notes

Reaction equation

HRID 1801295 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]=[CH:14][C:15]=1[F:16])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO.O>[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]=[CH:14][C:15]=1[F:16])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67442738Methyl 2-(3-benzamido-4-fluorophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate

Product 1

HCID 674417932-(3-Benzamido-4-fluorophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acidYield 44%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a round bottom flask, a mixture of methyl 2-(3-benzamido-4-fluorophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate (130 mg, 0.30 mmol) in methanol (3 mL) and water (0.6 mL) was treated with a solution of sodium hydroxide (204 mg, 5.1 mmol) in water (0.6 mL). The resultant mixture was heated for reflux for 1 h. The methanol was removed under vacuum. The residue was acidified with 1 M hydrochloric acid to pH=5. The precipitates were collected by filtration, purified by preparative Thin layer chromatography (silica gel, petroleum ether/ethyl acetate=2:1, 5% methanol) to afford 55 mg (44%) of 2-(3-benzamido-4-fluorophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid as a colorless solid. MS (ESI+APCI) M+1=419.

Workup

  1. temperaturefor reflux for 1 h
  2. customThe methanol was removed under vacuum
  3. filtrationThe precipitates were collected by filtration
  4. custompurified by preparative Thin layer chromatography (silica gel, petroleum ether/ethyl acetate=2:1, 5% methanol)

Sources & evidence

ORD record
ord-8c630fa3b89c4ee2a9e9e243c72345c7
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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