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

HRID 43591Notes

Reaction equation

HRID 43591 reaction equation
[N+:1]([C:4]1[CH:24]=[CH:23][C:7]2[N:8]([CH2:12][C:13]3[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=3)[CH2:9][CH2:10][O:11][C:6]=2[CH:5]=1)([O-])=O.CN(C=O)C>[Zn].O.O.O.O.O.O.[Fe](Cl)(Cl)Cl.O>[NH2:1][C:4]1[CH:24]=[CH:23][C:7]2[N:8]([CH2:12][C:13]3[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=3)[CH2:9][CH2:10][O:11][C:6]=2[CH:5]=1

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 67548570Methyl 4-[(7-nitro-2,3-dihydro-4H-1,4-benzoxazin-4-yl)methyl]benzoate

Product 1

HCID 28320862Methyl 4-[(7-amino-2,3-dihydro-4H-1,4-benzoxazin-4-yl)methyl]benzoateYield 87.7%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 16211236Trichloroiron;hexahydrateCatalystHCID 962WaterSolvent

Procedure

The same operation as in Example (100b) was performed using methyl 4-[(7-nitro-2,3-dihydro-4H-1,4-benzoxazin-4-yl)methyl]benzoate obtained in Example (101a) (0.35 g, 1.07 mmol), zinc (0.7 g, 10.7 mmol), iron trichloride hexahydrate (0.12 g, 0.4 mmol), DMF (5 mL) and water (5 mL), to obtain 0.28 g of the crude title compound as a brown oily substance (88%).

Sources & evidence

ORD record
ord-de25844bc9b849ed8e435b16766a4218
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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