5-Chloro-7-nitro-2,3-dihydro-1,3-benzoxazol-2-one → 7-Amino-2(3H)-benzoxazolone

Temperature

45 °C

107.5 g (1 mole) of 5-chloro-7-nitro-2(3H)-benzoxazolone prepared according to Example 1d was suspended in 1000 ml of ethanol. 9.25 g of Pd/C 5% and 50 ml of ethanol were added and the mixture was hydrogenated at 4 bar hydrogen pressure for four to six hours at 60-65° C. while vigorously stirring. When the hydrogenation was complete, the mixture was cooled to 45° C. and filtered over Hyflo®. The Hyflo® was washed twice with 175 ml of methanol. 500 ml of solvent was distilled off under reduced pressure at 50° C., followed by addition of 250 ml of water and removal of 300 ml of solvent was by distillation under reduced pressure at 50° C. The last procedure was repeated twice and finally 250 ml of water was added and 400 ml of solvent was distilled of. The resulting mixture was cooled to 0-5° C. in about one hour. The solid was filtered off and, washed three times with 125 ml of cold water, and dried at 50° C. and 100 mbar under a gentle nitrogen stream till dry. Yield about 94%.

1. filtrationfiltered over Hyflo®
2. washThe Hyflo® was washed twice with 175 ml of methanol
3. distillation500 ml of solvent was distilled off under reduced pressure at 50° C.
4. additionfollowed by addition of 250 ml of water and removal of 300 ml of solvent
5. distillationwas by distillation under reduced pressure at 50° C
6. additionfinally 250 ml of water was added
7. distillation400 ml of solvent was distilled of
8. temperatureThe resulting mixture was cooled to 0-5° C. in about one hour
9. filtrationThe solid was filtered off
10. washwashed three times with 125 ml of cold water
11. customdried at 50° C.
12. customtill dry

ORD record

ord-dd7f37d495744195ab2fb72dbcf8c2bd

Source dataset

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07405216B2