Ammonium Chloride → HCID 86727313, compound

Temperature

70 °C

To a solution of 4,7-dimethyl-6-nitro-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (0.085 g, 0.31 mmol) and ammonium chloride (0.164 g, 3.1 mmol) in MeOH (10 mL) and THF (10 mL) was added zinc powder (0.200 g, 3.1 mmol) and the resulting mixture was heated at 70° C. for 4 h. The reaction mixture was cooled to ambient temperature, filtered and the filtrate was washed with MeOH (15 mL). The filtrate was concentrated in vacuo and the residue was dissolved in water (20 mL). The aqueous solution was extracted with EtOAc (3×15 mL) and the combined organic phase was dried over anhydrous Na2SO4, filtered and concentrated to give 6-amino-4,7-dimethyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (0.060 g, 0.24 mmol, 79%) as a solid, which was used directly in the next step. TLC (eluting with 25% EtOAc in petroleum ether) Rf=0.2.

1. temperatureThe reaction mixture was cooled to ambient temperature
2. filtrationfiltered
3. washthe filtrate was washed with MeOH (15 mL)
4. concentrationThe filtrate was concentrated in vacuo
5. dissolutionthe residue was dissolved in water (20 mL)
6. extractionThe aqueous solution was extracted with EtOAc (3×15 mL)
7. dry with materialthe combined organic phase was dried over anhydrous Na2SO4
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-a1b259be2de94d5d9447f38d094d3526

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09115151B2