Methyl iodide → 6,9-Dimethyl-3-nitro-pyrido(2,3-b)(1,5)benzoxazepin-5(6H)-one

HRID 1078555Notes

Reaction equation

HRID 1078555 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:22]=[N:21][C:9]2[O:10][C:11]3[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:12]=3[NH:13][C:14](=[O:15])[C:8]=2[CH:7]=1)([O-:5])=[O:4].[CH3:23]I>CN(C)C=O>[N+:3]([C:6]1[CH:22]=[N:21][C:9]2[O:10][C:11]3[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:12]=3[N:13]([CH3:23])[C:14](=[O:15])[C:8]=2[CH:7]=1)([O-:5])=[O:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 15168935HCID 15168935, compound

Product 1

HCID 4539736,9-Dimethyl-3-nitro-pyrido(2,3-b)(1,5)benzoxazepin-5(6H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (0.73 g, 0.015 mol of a 50% dispersion in mineral oil) in dimethylformamide (75 ml) under argon was added in one portion 3-Nitro-9-methylpyrido[2,3-b][1,5]benzoxazepin-5(6H)-one (3.75 g, 0.014 mol). Methyl iodide (1.3 ml. 0.021 mol) was added, and the resulting solution was stirred overnight at room temperature. The mixture was diluted with ice Water, and the precipitated product was collected and washed with water and pet ether. The crude product was recrystallized from ethyl acetate to give 3.14 g (79% of theory) of the product as a pale yellow solid. m.p. 197°-198° C.

Workup

  1. customthe precipitated product was collected
  2. washwashed with water and pet ether
  3. customThe crude product was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-8fe03fd16ec04a4aa66c3633d3732bae
Source dataset
uspto-grants-1996_08
Patent number
US05550122

Reaction notes

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