Chloroform → N-allyl-5-azaisatoic anhydride

HRID 215790Notes

Reaction equation

HRID 215790 reaction equation
[C:1]12[C:7](=[CH:8][CH:9]=[N:10][CH:11]=1)[NH:6][C:5](=[O:12])[O:4][C:2]2=[O:3].[CH2:13](Br)[CH:14]=[CH2:15].C(N(CC)CC)C.C(Cl)(Cl)Cl>CN(C=O)C>[CH2:15]([N:6]1[C:5](=[O:12])[O:4][C:2](=[O:3])[C:1]2=[CH:11][N:10]=[CH:9][CH:8]=[C:7]12)[CH:14]=[CH2:13]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 7841Allyl bromideHCID 8471TriethylamineHCID 107970962H-Pyrido[4,3-d][1,3]oxazine-2,4(1H)-dione

Product 1

HCID 86595201N-allyl-5-azaisatoic anhydride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-azaisatoic anhydride (1 mmol, Coppola, G. M. Synthesis 1980, 505) and allyl bromide (1.1 mmol) in DMF is added triethylamine (1.2 mmol) dropwise. The reaction mixture is allowed to stir at room temperature for 12 h after which time CHCl3 is added and the organic layer is washed with water, dried (MgSO4) and the solvent is evaporated to give N-allyl-5-azaisatoic anhydride.

Workup

  1. additionis added
  2. washthe organic layer is washed with water
  3. dry with materialdried (MgSO4)
  4. customthe solvent is evaporated

Sources & evidence

ORD record
ord-6d46e73ce85047f2bab5e918a410ba72
Source dataset
uspto-grants-2012_06
Patent number
US08193185B2

Reaction notes

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