Sodium hydride → Methyl 4-[(7-nitro-2,3-dihydro-4H-1,4-benzoxazin-4-yl)methyl]benzoate

HRID 43590Notes

Reaction equation

HRID 43590 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][C:7]2[NH:8][CH2:9][CH2:10][O:11][C:6]=2[CH:5]=1)([O-:3])=[O:2].[H-].[Na+].Br[CH2:17][C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=1>CN(C=O)C>[N+:1]([C:4]1[CH:13]=[CH:12][C:7]2[N:8]([CH2:17][C:18]3[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=3)[CH2:9][CH2:10][O:11][C:6]=2[CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 256687Methyl 4-(bromomethyl)benzoateHCID 184161517-Nitro-3,4-dihydro-2H-1,4-benzoxazine

Product 1

HCID 67548570Methyl 4-[(7-nitro-2,3-dihydro-4H-1,4-benzoxazin-4-yl)methyl]benzoateYield 90.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The same operation as in Example (90a) was performed using 7-nitro-2,3-dihydro-4H-1,4-benzoxazine (described in Higuchi, Robert I.; Arienti, Kristen L.; Lopez, Francisco J.; Mani, Neelakhanda S.; Mais, Dale E.; Caferro, Thomas R.; Long, Yun Oliver; Jones, Todd K.; Edwards, James P.; Zhi, Lin; Schrader, William T.; et al.; J. Med. Chem.; 50; 10; 2007; 2486-2496, 0.6 g, 3.3 mmol), sodium hydride (55% content, 145 mg, 3.3 mmol), methyl 4-bromomethylbenzoate (0.76 g, 3.3 mmol) and DMF (20 mL). The resulting solid was washed with ethyl acetate/hexane=1/1 to obtain 0.98 g of the title compound as a yellow solid (90%).

Workup

  1. washThe resulting solid was washed with ethyl acetate/hexane=1/1

Sources & evidence

ORD record
ord-b623cd7a72004e8c98dc9f0aa80c8b0e
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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