2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 2-((Propan-2-yl)amino)benzaldehyde
Reaction equation
[CH:1]([NH:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH2:7][OH:8])([CH3:3])[CH3:2].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O1CCOCC1>[CH:1]([NH:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH:7]=[O:8])([CH3:3])[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 9.6 g of 2-isopropylaminobenzyl alcohol in 200 ml of dioxane was added 13.2 g of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) in several portions, followed by stirring for an hour. The solvent was evaporated, the reaction solution was concentrated, and methylene chloride was added thereto, followed by filtration. The filtrate was concentrated, and the resulting oily substance was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1) to give 7.6 g of 2-isopropylaminobenzaldehyde.