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

HRID 1425064Notes

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

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

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

Sources & evidence

ORD record: ord-2476bce55f1a439fa533f9ed571bca14
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08927588B2

Reaction notes

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