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

HRID 1425068Notes

Reaction equation

HRID 1425068 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-3ee5b1fe9266478fbb0de9becb8714da
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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