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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 43587Generated: October 25, 2026

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

https://huagongshe.com/reaction/43587

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantMethyl 3-[(7-nitro-2,3-dihydro-4H-1,4-benzoxazin-4-yl)methyl]benzoateHCID 67548908—
CatalystZincHCID 23994—
CatalystTrichloroiron;hexahydrateHCID 16211236—
SolventWaterHCID 962—
ProductMethyl 3-[(7-amino-2,3-dihydro-4H-1,4-benzoxazin-4-yl)methyl]benzoateHCID 6754906187.7%

Reaction Conditions

Temperature100 °C

Reaction Steps

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%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08536197B2
Source datasetuspto-grants-2013_09
ORD IDord-47c782a9394549e481b52eb2e7a2fe4e
Source noteuspto-grants-2013_09