HCID 86751457, compound → Cryptolepine

Participants

Reaction Steps

5-Methylquindolinium hydroiodide (1.5 g, 4.2 mmol) from Example 3 was shaken with a 5% solution of Na2CO3 (100 mL) and extracted with chloroform (2×200 mL). The extract of the free base was purified on a basic alumina column using chloroform to elute the quindoline impurity; elution with 1-2% methanol in chloroform gave 0.5 g of the title compound as a purple solid, mp 178-180° C. [lit 166-169° C. (Gellert, E.; Raymond-Hamet; Schlittler, E. Helv. Chim. Acta 1951, 34, 642-651)]; 1H NMR (DMSO-d6) δ 8.92 (s, H11), 8.50 (d, J=9.2, 1H, H4), 8.47 (d, J=8.4, 1H, H6), 8.38 (d, J=8.4, 1H, H1), 7.89 (t, J=7.6, 1H, H3), 7.69-7.64 (m, 2H, H2 and H9), 7.52 (t, J=8.4, 1H, H8), 7.02 (t, J=8.4, 1H, H7), 4.90 (s, 3H, NCH3); 13C NMR (DMSO-d6) δ 160.46, 144.76, 138.96, 132.56, 130.13, 129.47, 128.66, 126.15, 124.97, 124.26, 123.60, 119.30, 116.36, 116.23, 113.64, 38.73.

Provenance & Evidence