Water → HCID 59441786, compound

Participants

Reaction Steps

A 0° C. orange solution of (2S)-1-acetyl-2-methyl-5-(methyloxy)-2,3-dihydro-1H-indole (5.19 g, 25.3 mmol) in TFA (30 mL) was treated with NaNO2 (1.745 g, 25.3 mmol) portion wise. After 2 h more NaNO2 (800 mg, 11.6 mmol) was added. After 1 h the resulting mixture was poured into water (450 mL). The resulting slurry was filtered and the solids were washed with water. The solids were dissolved in CH2Cl2. The layers were separated, the organic layer was dried (Na2SO4) and concentrated to afford (2S)-1-acetyl-2-methyl-5-(methyloxy)-6-nitro-2,3-dihydro-1H-indole as a green solid (5.73 g, 91%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.23 (d, J=6.23 Hz, 3H), 2.22 (s, 3H), 2.76 (d, J=17.21 Hz, 1H), 3.45 (dd, J=17.03, 8.97 Hz, 1H), 3.89 (s, 3H), 4.58-4.78 (m, 1H), 7.35 (s, 1H), 8.41 (s, 1H); ESIMS (M+H)+=251.02.

Provenance & Evidence