Potassium Carbonate → N'-hydroxy-1-methyl-5-nitro-1H-pyrazole-3-carboximidamide

To a solution of 1-methyl-5-nitro-1H-pyrazole-3-carbonitrile (2.4 g, 15.8 mmol, Princeton) and hydroxylamine hydrochloride (3.29 g, 47.3 mmol) in EtOH (0.50 mL) was added potassium carbonate (10.9 g, 79 mmol) and the mixture was refluxed for about 2 h. The reaction mixture was filtered hot and the collected solid was rinsed with EtOH (50 mL) and then MeOH (100 mL). The filtrate was concentrated under reduced pressure. The crude material was partitioned between DCM (40 mL) and water (20 mL). The aqueous layer was acidified to about pH 2 using 1 N HCl and back extracted with DCM (20 mL). The aqueous layer was basified using saturated NaHCO3 and the precipitate was collected by vacuum filtration and dried to afford N′-hydroxy-1-methyl-5-nitro-1H-pyrazole-3-carboximidamide (1.24 g, 4.49 mmol, 67%). LC-MS (Table 1, Method g) Rt=1.07 min, m/z 186 (M+H)+. 1H-NMR (DMSO-d6, Bruker 400 MHz) δ 9.78 (s, 1H), 7.22 (s, 1H), 5.71 (s, 2H), 4.16 (s, 3H).

1. temperaturethe mixture was refluxed for about 2 h
2. filtrationThe reaction mixture was filtered hot
3. washthe collected solid was rinsed with EtOH (50 mL)
4. concentrationThe filtrate was concentrated under reduced pressure
5. customThe crude material was partitioned between DCM (40 mL) and water (20 mL)
6. extractionback extracted with DCM (20 mL)
7. filtrationthe precipitate was collected by vacuum filtration
8. customdried

ORD record

ord-0b48984199de4a0694894b0d151c1a8d

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09150592B2