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

HRID 1801289Notes

Reaction equation

HRID 1801289 reaction equation
[F:1][C:2]1[CH:32]=[CH:31][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([CH:15]3[C:24]([CH3:26])([CH3:25])[CH2:23][C:22]4[C:17](=[CH:18][CH:19]=[C:20]([C:27]([O:29]C)=[O:28])[CH:21]=4)[NH:16]3)=[CH:11][CH:10]=2)=[O:7])=[CH:4][CH:3]=1.[OH-].[Na+]>CO.O>[F:1][C:2]1[CH:32]=[CH:31][C:5]([C:6]([NH:8][C:9]2[CH:10]=[CH:11][C:12]([CH:15]3[C:24]([CH3:26])([CH3:25])[CH2:23][C:22]4[C:17](=[CH:18][CH:19]=[C:20]([C:27]([OH:29])=[O:28])[CH:21]=4)[NH:16]3)=[CH:13][CH:14]=2)=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67441009Methyl 2-(4-(4-fluorobenzamido)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate

Product 1

HCID 674427482-(4-(4-Fluorobenzamido)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acidYield 95%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a mixture of methyl 2-(4-(4-fluorobenzamido)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate (43 mg, 0.01 mmol) in methanol (3 mL) and water (1.5 mL) was add a solution of sodium hydroxide (68 mg, 0.17 mmol.) in water (1.5 mL). The resultant mixture was heated to reflux until the completion of the reaction (monitored by thin layer chromatography). The methanol was removed under vacuum. The residue was acidified with 2 M hydrochloric acid to pH=1. The precipitates were collected by filtration to afford 2-(4-(4-fluorobenzamido)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid as a yellow solid, 40 mg, Yield 95% MS (ESI+APCI) M+1=419.6.

Workup

  1. temperatureto reflux until the completion of the reaction (monitored by thin layer chromatography)
  2. customThe methanol was removed under vacuum
  3. filtrationThe precipitates were collected by filtration

Sources & evidence

ORD record
ord-e0aa95244a044a6081340e25fbaf103e
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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