Pyridine → HCID 10524870, compound

Participants

Reaction Steps

To a mixture of 2-nitro-4-(dimethyl-t-butylsiloxy)aniline (10.01 g, 37.30 mmol) and CH2Cl2 (400 mL) at 0° C was added pyridine (3.4 mL, 42.0 mmol) followed by the 3-cyanobenzoyl chloride (8.65 g, 52.2 mmol). The reaction was allowed to warm to room temperature and stirred for 1 h. The reaction was diluted with CH2Cl2 (800 mL) and washed with sat. aq. NH4Cl (2×200 mL). The organic layer was MgSO4 dried, filtered, and concentrated. The residue was chromatographed (20% EtOAc/hexanes) to give the title compound as a solid (13.94 g, 94%); IR(CHCl3): 2932, 1689, 1508, 1289, 863 cm−1; NMR(300 MHz, CDCl3): δ0.27 (s, 6H), 1.02 (s, 9H), 7.27 (s, 1H), 7.70 (m, 2H), 7.90 (d, J=7.8, 1H), 8.16 (d, J=1.2, 1H), 8.30 (s, 1H), 8.79 (d, J=9.3, 1H), 11.15 (br s, 1H); MS(FD): 397.0.

Provenance & Evidence