Water → HCID 44549536, compound

Participants

Reaction Steps

A solution of 184 (100 mg, 0.24 mmol) and Cs2CO3 (312 mg, 0.96 mmol) in MeOH (10 mL) and CH2Cl2 (15 mL) was stirred for 1.5 h. Water was added and the mixture was extracted with CH2Cl2 (×3). The combined organic extracts were washed with water, brine and dried. The solvent was evaporated and the residue was dissolved in CH2Cl2MeOH and, solvents were evaporated under reduced pressure until precipitation began. The precipitate was filtered off and washed with MeOH to give methyl 1-(chloromethyl)-5-nitro-1,2-dihydro-3H-benzo[e]indole-8-carboxylate (186) (76 mg, 100%): mp 161-163° C.; 1H NMR [(CD3)2SO] δ 8.40 (dd, J=1.6, 0.6 Hz, 1H), 8.22 (dd, J=9.1, 0.4 Hz, 1H), 7.82 (dd, J=9.1, 1.7 Hz, 1H), 7.78 (s, 1H), 6.49 (d, J=1.6 Hz, 1H), 4.35-4.28 (m, 1H), 3.93 (s, 3H), 3.89-3.82 (m, 2H), 3.79-3.69 (m, 2H). HRMS (CI) calcd. for C15H1335ClN2O4 (M+) m/z 320.0534, found 320.0563.

Provenance & Evidence