Hydrazine, dihydrochloride → HCID 178419301, compound

Temperature

100 °C

To a suspension of 8-bromo-4-[1-dimethylamino-meth-(E)-ylidene]-3,4-dihydro-2H-benzo[b]-oxepin-5-one (5.32 g, 17.9 mmol) in isopropyl alcohol (50 mL) was added powdered hydrazine dihydrochloride (3.77 g, 35.9 mmol) at room temperature, then the mixture stirred for 2 h. The reaction mixture was diluted with water (20 mL) and then heated at 100° C. for 2 h before cooling to room temperature. The reaction mixture was concentrated in vacuo to remove the volatile solvent. The resulting suspension was filtered and the filtrate washed with water and dried under vacuum at 40° C. to yield 8-Bromo-4,5-dihydro-2H-6-oxa-1,2-diaza-benzo[e]azulene as a pale yellow solid (4.28 g, 90%). 1H NMR δ (ppm)(DMSO-d): 8.07 (1 H, d, J=8.52 Hz), 7.64 (1 H, s), 7.30-7.24 (1 H, m), 7.21 (1 H, d, J=2.07 Hz), 4.24 (2 H, dd, J=5.63, 4.50 Hz), 3.00 (2 H, t, J=5.09 Hz).

1. temperaturebefore cooling to room temperature
2. concentrationThe reaction mixture was concentrated in vacuo
3. customto remove the volatile solvent
4. filtrationThe resulting suspension was filtered
5. washthe filtrate washed with water
6. customdried under vacuum at 40° C.

ORD record

ord-8ce54a9bfb9447daa3ae32b4304ef70e

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08785626B2