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

HRID 43587Notes

Reaction equation

HRID 43587 reaction equation
CN(C=O)C.[N+:6]([C:9]1[CH:29]=[CH:28][C:12]2[N:13]([CH2:17][C:18]3[CH:19]=[C:20]([CH:25]=[CH:26][CH:27]=3)[C:21]([O:23][CH3:24])=[O:22])[CH2:14][CH2:15][O:16][C:11]=2[CH:10]=1)([O-])=O>[Zn].O.O.O.O.O.O.[Fe](Cl)(Cl)Cl.O>[NH2:6][C:9]1[CH:29]=[CH:28][C:12]2[N:13]([CH2:17][C:18]3[CH:19]=[C:20]([CH:25]=[CH:26][CH:27]=3)[C:21]([O:23][CH3:24])=[O:22])[CH2:14][CH2:15][O:16][C:11]=2[CH:10]=1

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 67548908Methyl 3-[(7-nitro-2,3-dihydro-4H-1,4-benzoxazin-4-yl)methyl]benzoate

Product 1

HCID 67549061Methyl 3-[(7-amino-2,3-dihydro-4H-1,4-benzoxazin-4-yl)methyl]benzoateYield 87.7%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 16211236Trichloroiron;hexahydrateCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

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%).

Workup

  1. filtrationThe insoluble matter was filtered off
  2. additionethyl acetate was added to the mother liquor
  3. washthe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-47c782a9394549e481b52eb2e7a2fe4e
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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