Ammonium Chloride → HCID 69652717, compound

To a mixture of 1-(2,2-dimethoxyethyl)-6-nitro-2H-indazole (1.89 g, 7.52 mmol) and NH4Cl (337 mg, 6.01 mmol) in ethanol/H2O (2:1, 75 mL) at room temperature was added Fe (1.28 g, 23.7 mmol) and the mixture was heated for 2 hours at 70 C. The mixture was cooled to room temperature, filtered through celite, which was washed with hot methanol (5×20 mL), and the combined filtrate concentrated under reduced pressure. The residue was diluted with ethyl acetate (50 mL), filtered, the filtrate was concentrated under reduced pressure to provide 1-(2,2-dimethoxyethyl)-2H-indazol-6-ylamine as an amber oil. 1H NMR (300 MHz, DMSO-d6) δ ppm 3.26 (m, 6 H), 4.23 (d, J=5.42 Hz, 2 H), 4.71 (t, J=5.42 Hz, 1 H), 5.30 (s, 2 H), 6.49 (m, 2 H), 7.35 (m, 1 H), and 7.73 (s, 1 H); MS (ESI) 222 (M+H)+.

1. temperaturethe mixture was heated for 2 hours at 70 C
2. filtrationfiltered through celite, which
3. washwas washed with hot methanol (5×20 mL)
4. concentrationthe combined filtrate concentrated under reduced pressure
5. additionThe residue was diluted with ethyl acetate (50 mL)
6. filtrationfiltered
7. concentrationthe filtrate was concentrated under reduced pressure

ORD record

ord-818e4ca598ff4a3cb2d249174af30651

Source dataset

uspto-grants-2006_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07071182B2