Phosphoric Acid → HCID 69055426, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1-((4-methoxy-2,3-dimethylphenylamino)methyl)cyclobutanecarboxylic acid (19 g in toluene (100 mL) was added into phosphoric acid (25 mL). The mixture was heated up in a 116° C. bath and stirred for an hour. The mixture was then cooled down, quenched with ice, and extracted with ethylacetate. The organic phase was then dried and evaporated to dryness. The crude product was passed through a column (Hexane: EtOAc; 10:4) to give 6′-methoxy-7′,8′-dimethyl-1′H-spiro[cyclobutane-1,3′-quinolin]-4′(2′H)-one (15 g) as a yellow solid. 1H-NMR (300 MHz, CDCl3): δ=7.26 (s, 1H), 4.11 (s, 1H), 3.79 (s, 3H), 3.54 (s, 2H), 2.59-2.29 (m, 2H), 2.38 (3H), 2.34 (3H), 2.06-1.82 (4H) ppm. 13C-NMR (75 MHz, CDCl3) δ=196.22, 150.49, 144.93, 133.95, 122.36, 115.05, 104.75, 55.77, 51.45, 46.5, 25.95, 15.06, 12.98, 12.77 ppm.

Provenance & Evidence