Hydrogen Peroxide → HCID 178440202, compound

To a suspension of 48.94 g (0.3 mol) of 3-nitro-5-amino-benzonitrile in 500 ml of CH2Cl2 was added 63 ml of Et3N, 3 g DMAP and lastly, dropwise, 45.5 g (0.45 mol) of butyryl chloride. A mild exothermic reaction ensued. The mixture was allowed to stir for 2 days (monitor TLC with 50% EtOAc/hexanes). The solution was washed with 1N HCl (2×100 ml), water (1×100 ml) sat. NaHCO3 (2×100 ml), brine (1×100 ml) and dried over MgSO4. The suspension was filtered and concentrated in vacuo. The residue was suspended in a mixture of 600 ml of MeOH and 200 ml of water in a three neck round bottom flask. To this was added gradually 140 ml (0.7 m) of 5N NaOH solution followed by the dropwise addition of 80 ml of 30% H2O2 (0.7 mol) solution (beware of exothermic reaction!). The mixture was refluxed over night, cooled to room temperature and filtered. The filtrate was acidified with 1N HCl cooled to 5° C. and filtered. The quinazolinone may be recrystallized form hot MeOH to give 38 g of pale brown free crystals. 54% yield. 1H-NMR-CDCl3 : 1.10 (t, 3H, J=7.8 Hz), 1.93 (m, 2H), 2.79 (t, 2H, J=7.3 Hz), 7.81 (d, 1H, J=8.9 Hz), 8.55 (dd, 1H, J=2.4, 8.8 Hz), 9.14 (d, 1H, J=2.4 Hz), 10.72 (bs, 1H).

1. customA mild exothermic reaction
2. washThe solution was washed with 1N HCl (2×100 ml), water (1×100 ml) sat. NaHCO3 (2×100 ml), brine (1×100 ml)
3. dry with materialdried over MgSO4
4. filtrationThe suspension was filtered
5. concentrationconcentrated in vacuo
6. additionThe residue was suspended in a mixture of 600 ml of MeOH and 200 ml of water in a three neck round bottom flask
7. additionTo this was added gradually 140 ml (0.7 m) of 5N NaOH solution
8. temperatureThe mixture was refluxed over night
9. filtrationfiltered
10. temperaturecooled to 5° C.
11. filtrationfiltered
12. customThe quinazolinone may be recrystallized form hot MeOH

ORD record

ord-8c3937ec06c145889fe9152f47f96d94

Source dataset

uspto-grants-1995_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05409926