Hydrazine hydrate (1:1) → HCID 86727620, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(6-nitro-3-thioxo-2,3-dihydro-benzo[1,4]oxazin-4-yl)-propionic acid ethyl ester (133.0 g, 450 mmol) in EtOH (1.5 L) was added hydrazine hydrate (45.0 g, 900 mmol, 98%) and the mixture was heated to 80° C. and stirred for 3 h. The reaction mixture was cooled to ambient temperature and filtered. The filtrate was washed with cold EtOH (3×50 mL) to give 4-methyl-6-nitro-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one as a yellow solid (80.0 g, 68%). 1H NMR (DMSO-d6, 400 MHz): δ 10.91 (s, 1H), 7.98 (d, J=2.8 Hz, 1H), 7.86 (dd, J=2.8 Hz, J=8.8 Hz, 1H), 7.23 (d, J=8.8 Hz, 1H), 4.99 (q, J=6.4 Hz, 1H), 4.78 (d, J=12.8 Hz, 2H), 1.36 (d, =6.8 Hz, 3H).

Provenance & Evidence