Sodium Hydroxide → HCID 70495643, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2′-(3-morpholinophenyl)-2′,3′-dihydro-1′H-spiro[cyclopentane-1,4′-quinoline]-6′-carboxylic acid methyl ester (406.0 mg, 1.0 mmol) in tetrahydrofuran (10.0 mL) and methanol (10.0 mL) was added 3 N sodium hydroxide (2.0 mL). The reaction mixture was stirred at 80° C. for 6 h, and then diluted with water (10.0 mL), extracted with diethyl ether (20.0 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). The combined organic layers were dried over anhydrous sodium sulfate. The solvent was removed in vacuo and afforded 2′-(3-morpholinophenyl)-2′,3′-dihydro-1′H-spiro[cyclopentane-1,4′-quinoline]-6′-carboxylic acid (352.8 mg, 90%) as a light yellow powder: MS (ESI) M+1=393.1.

Provenance & Evidence