Sodium Hydroxide → 2-(2,5-Dichloro-phenyl)-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid

HRID 2047696Notes

Reaction equation

C[O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]([C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[Cl:22])[CH2:9][C:8]2([CH3:24])[CH3:23])=[O:4].[OH-].[Na+]>O1CCCC1.CO.O>[Cl:22][C:16]1[CH:17]=[CH:18][C:19]([Cl:21])=[CH:20][C:15]=1[CH:10]1[CH2:9][C:8]([CH3:23])([CH3:24])[C:7]2[C:12](=[CH:13][CH:14]=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=2)[NH:11]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-(2,5-dichloro-phenyl)-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid methyl ester (1.0 g, 2.8 mmol) in tetrahydrofuran (8 mL) and methanol (8 mL) was added 3N sodium hydroxide (5 mL). The reaction mixture was stirred at 80° C. for 4 hours, and then diluted with water (10 mL), extracted with diethyl ether (20 mL). The organic layer was discarded. The aqueous layer was acidified with concentrated hydrochloric acid to pH 4 and extracted with ethyl acetate (40 mL×3), and the combined organics were dried over anhydrous Na2SO4. The solvent was removed in vacuo and purified by preparative HPLC to afford 2-(2,5-dichloro-phenyl)-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (600 mg, 61.4%) as a yellow foam. MS (ESI+) [(M+H)+] 350.1.

Workup

extractionextracted with diethyl ether (20 mL)
extractionextracted with ethyl acetate (40 mL×3)
dry with materialthe combined organics were dried over anhydrous Na2SO4
customThe solvent was removed in vacuo
custompurified by preparative HPLC

Sources & evidence

ORD record: ord-f6b6760c623a42fea9585606f9573fc9
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592594B2

Reaction notes

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