Methylamine → HCID 20746075, compound

Participants

Reaction Steps

A 2.0 M solution of methylamine in THF (25 ml, 50 mmole) was added to a solution of 2-methyl-5-nitro-1-(4-nitrophenoxycarbonyl)indole 1a (2.11 g, 6.2 mmole) in THF (240 ml). The resultant reaction mixture was stirred at ambient temperature for 4 hours prior to removal of the solvent by concentration, in vacuo. The residue obtained was partitioned between EtOAc (200 ml) and H2O (200 ml). The layers were separated and the aqueous phase was extracted with EtOAc (2×100 ml). The combined organic extracts were washed with sat'd NaHCO3 (150 ml), dried over Na2SO4 and concentrated, in vacuo, to give a yellow solid which was suspended in Et2O (35 ml), filtered and washed with Et2O (2×20 ml) to give 1.17 g (81%) of a pale yellow solid. 1H NMR (DMSO-d6): δ 8.52 (1H, q, J=4.5 Hz), 8.46 (1H, d, J=2.3 Hz), 8.03 (1H, dd, J=2.3, 9.1 Hz), 7.71 (1H, d, J=9.1 Hz), 6.62 (1H, s), 2.89 (3H, d, J=4.5 Hz), 2.51 (3H, s). Anal. Calcd. for C11H13N3O3: C, 56.65; H, 4.75; N, 18.02. Found: C, 56.56; H, 4.78; N, 17.82.

Provenance & Evidence