Sodium Hydroxide → HCID 69673439, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 2-(2-methyl-4-p-tolyl-7,8-dihydro-6H-cyclopenta[g]quinolin-3-yl)pentanoate and methyl 2-(3-methyl-4-p-tolyl-8,9-dihydro-6H-cyclopenta[g]quinolin-3-yl)pentanoate (0.316 g; 0.81 mmol) in a mixture methanol-ethanol (2:1) (24 mL) was added a 5% sodium hydroxide solution (24.46 mmol; 19.5 mL) and the reaction mixture was heated to 60° C. for 18 h. The organic volatiles were removed under reduced pressure and the remaining basic solution was acidified to pH 2 with a 1N hydrochloric solution and the aqueous layer was extracted with ethyl acetate. The organics were combined, dried over magnesium sulfate and concentrated under reduced pressure. Purification by preparative HPLC (method 1) furnished 0.003 g (1%) of 2-(3-methyl-1-p-tolyl-8,9-dihydro-7H-cyclopenta[f]quinolin-2-yl)pentanoic acid. ESI/APCI(+): 374 (M+H). 1H NMR (CDCl3) δ 7.90 (d, J=8.35 Hz, 1H, H-9); 7.53 (d, J=8.35 Hz, 1H, H-8); 7.27 (bs, 1H, H-6′); 7.26 (bs, 1H, H-5′); 7.25 (d, J=8.2 Hz, 1H, H-3′); 7.06 (d, J=8.2 Hz, 1H, H-2′); 3.83 (t, J=6.7 Hz, 1H, H-12); 2.89, (m, 2H, H-7); 2.72 (s, 3H, H-10); 2.47 (s, 3H, H-7′); 2.22 (m, 1H, H-5); 2.18 (m, 1H, H-13); 2.02 (m, 1H, H-5); 1.84 (m, 1H, H-6); 1.76 (m, 1H, H-6); 1.63 (m, 1H, H-13); 1.19 (m, 1H, H-14); 0.97 (m, 1H, H-14); 0.737 (t, J=7.3 Hz, 3H, H-15). 13C NMR (CDCl3) δ 177.4 (C-11); 155.7 (C-2); 148.1 (C-4); 145.4 (C-9a); 143.1 (C-7a); 139.8 (C-4b); 137.9 (C-4′); 136.6 (C-1′); 131.5 (C-3); 129.8 (C-2′); 129.7 (C-3′); 128.9 (C-6′); 128.5 (C-5′); 126.7 (C-9); 126.6 (C-8); 124.1 (C-4a); 46.04 (C-12); 34.12 (C-5); 33.12 (C-7); 32.77 (C-13); 25.25 (C-6); 23.50 (C-10); 21.44 (C-14); 21.40 (C-7′); 14.14 (C-15).

Provenance & Evidence