Hydrochloric Acid → 2-(4'-Tert-butyl-5-fluoro-biphenyl-3-yl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid

HRID 1800980

Reaction equation

C([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]([C:16]1[CH:17]=[C:18]([C:23]3[CH:28]=[CH:27][C:26]([C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:25][CH:24]=3)[CH:19]=[C:20]([F:22])[CH:21]=1)[C:10]([CH3:34])([CH3:33])[CH2:9]2)=[O:5])C.Cl>C(O)C.O1CCCC1.[OH-].[Na+].O>[C:29]([C:26]1[CH:25]=[CH:24][C:23]([C:18]2[CH:19]=[C:20]([F:22])[CH:21]=[C:16]([CH:11]3[C:10]([CH3:34])([CH3:33])[CH2:9][C:8]4[C:13](=[CH:14][CH:15]=[C:6]([C:4]([OH:5])=[O:3])[CH:7]=4)[NH:12]3)[CH:17]=2)=[CH:28][CH:27]=1)([CH3:32])([CH3:30])[CH3:31]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 2-(4′-tert-butyl-5-fluoro-biphenyl-3-yl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (0.17 g, 0.37 mmol) in ethanol (3 mL) and tetrahydrofuran (5 mL), 30% sodium hydroxide in water (1 mL) was stirred at 60° C. for 12 h. The mixture was neutralized with a 3 N aqueous hydrochloric acid solution and extracted with ethyl acetate (2×50 mL), washed with water, dried over anhydrous sodium sulfate and then concentrated in vacuo to afford 2-(4′-tert-butyl-5-fluoro-biphenyl-3-yl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (0.13 g, 80%) as a white solid which was used for next step without further purification: LC/MS m/e calcd for C28H30FNO2 (M+H)+: 432.6, observed: 432.3;

Workup

extractionextracted with ethyl acetate (2×50 mL)
washwashed with water
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-a61119a6fe6546da9ad3b7c263eb1277
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08344137B2

Linked notes

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