Reacción #606146

Ecuación de reacción

4,7-dimethyl-6-nitro-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one

ammonium chloride

→

6-amino-4,7-dimethyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one

Rendimiento 79.0%

Disolventes

MeOH

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction mixture was cooled to ambient temperature
2. 2
   Filtraciónfiltered
3. 3
   Lavadothe filtrate was washed with MeOH (15 mL)
4. 4
   ConcentraciónThe filtrate was concentrated in vacuo
5. 5
   workup.DISSOLUTIONthe residue was dissolved in water (20 mL)
6. 6
   ExtracciónThe aqueous solution was extracted with EtOAc (3×15 mL)
7. 7
   Secadothe combined organic phase was dried over anhydrous Na2SO4
8. 8
   Filtraciónfiltered
9. 9
   Concentraciónconcentrated

Procedimiento

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.

Fuente