2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 2-((Propan-2-yl)amino)benzaldehyde

HRID 3146

Reaction equation

HRID 3146 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

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 10797123[2-(Propan-2-ylamino)phenyl]methanol

Product 1

HCID 110410352-((Propan-2-yl)amino)benzaldehydeYield 80.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

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.

Workup

  1. customThe solvent was evaporated
  2. concentrationthe reaction solution was concentrated
  3. additionmethylene chloride was added
  4. filtrationfollowed by filtration
  5. concentrationThe filtrate was concentrated
  6. customthe resulting oily substance was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-8547a040ad9a425c98f22d4b4c6c403c
Source dataset
uspto-grants-1998_03
Patent number
US05733917

Linked notes

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