Water → N-allyl-5-azaisatin
Reaction equation
[CH2:1]([N:4]1[C:10](=O)[O:9][C:7](=[O:8])[C:6]2=[CH:12][N:13]=[CH:14][CH:15]=[C:5]12)[CH:2]=[CH2:3].[C-]#N.[K+].O>CN(C=O)C>[CH2:1]([N:4]1[C:5]2[C:6](=[CH:12][N:13]=[CH:14][CH:15]=2)[C:7](=[O:8])[C:10]1=[O:9])[CH:2]=[CH2:3]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
A solution of N-allyl-5-azaisatoic anhydride (20 mmol) in DMF is added dropwise to a suspension of pulverized potassium cyanide (21 mmol) in DMF at 100° C. The reaction mixture is stirred at 100° C. for an additional 5 min after which time the mixture is poured into cold water and extracted with ether. The organic layer is dried (Na2SO4), filtered and the solvent is removed. Stirring the resulting residue in 2N hydrochloric acid overnight and adjusting the pH to 7 gives, upon filtration, N-allyl-5-azaisatin.
Workup
- extractionextracted with ether
- dry with materialThe organic layer is dried (Na2SO4)
- filtrationfiltered
- customthe solvent is removed
- stirringStirring the resulting residue in 2N hydrochloric acid overnight
Sources & evidence
- ORD record
- ord-73d14aadc710400d916cae8a91c7e0a6
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08193185B2
Reaction notes
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