Benzyl Bromide → 1-Benzyl-6-methyl-isatoic anhydride

HRID 36041

Reaction equation

HRID 36041 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[NH:12][C:11](=[O:13])[O:10][C:8](=[O:9])[C:7]=12.[H-].[Na+].[H][H].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C=O)C>[CH2:18]([C:7]12[C:2]([CH3:1])=[CH:3][CH:4]=[CH:5][CH:6]1[NH:12][C:11](=[O:13])[O:10][C:8]2=[O:9])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 104875225-methyl-2,4-dihydro-1H-3,1-benzoxazine-2,4-dioneHCID 178418361HCID 178418361, compound

Product 1

HCID 867464321-Benzyl-6-methyl-isatoic anhydride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
45 °C

Procedure

A solution of 6-methyl-isatoic anhydride (4.5 gm) in DMF (30 ml) was added dropwise to a stirred suspension of 60% sodium hydride (1.0 gm) in DMF (20 ml) under nitrogen atmosphere. The reaction was then warmed to 45° C. and stirred until hydrogen evolution ceased. It was then cooled and a solution of benzyl bromide (4.4 gm) in DMF (10 ml) was added slowly. Stirring was continued for one hour at room temperature and the solution was then evaporated under reduced pressure at 45° C. The resulting solid was suspended in methylene chloride, the insoluble inorganic solid was removed by filtration and the filtrate was evaporated to give 1-benzyl-6-methyl-isatoic anhydride as a crystalline solid.

Workup

  1. temperatureIt was then cooled
  2. customthe solution was then evaporated under reduced pressure at 45° C
  3. customthe insoluble inorganic solid was removed by filtration
  4. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-4c452b40dc494b31bb3fc9080edf4bf9
Source dataset
uspto-grants-1995_05
Patent number
US05412104

Linked notes

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