Reaction #71865

Reaction equation

DMF

methyl 3-[(7-nitro-2,3-dihydro-4H-1,4-benzoxazin-4-yl)methyl]benzoate

Methyl 3-[(7-nitro-2,3-dihydro-4H-1,4-benzoxazin-4-yl)methyl]benzoate

→

crude title compound

Yield 87.7%

Methyl 3-[(7-amino-2,3-dihydro-4H-1,4-benzoxazin-4-yl)methyl]benzoate

Yield 87.7%

Solvents

water

Conditions

Workup

1. 1
   FiltrationThe insoluble matter was filtered off
2. 2
   workup.ADDITIONethyl acetate was added to the mother liquor
3. 3
   Washthe organic layer was washed with water and brine
4. 4
   Dryingdried over anhydrous magnesium sulfate
5. 5
   ConcentrationConcentration under reduced pressure

Procedure

DMF (5 mL), water (5 mL), zinc (0.7 g, 10.7 mmol) and iron trichloride hexahydrate (0.12 g, 0.4 mmol) were added to methyl 3-[(7-nitro-2,3-dihydro-4H-1,4-benzoxazin-4-yl)methyl]benzoate obtained in Example (100a) (0.35 g, 1.07 mmol), and the mixture was stirred at 100° C. for 50 minutes. The insoluble matter was filtered off and ethyl acetate was added to the mother liquor, and the organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. Concentration under reduced pressure gave 0.28 g of the crude title compound as a brown oily substance (88%).

Source