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

HRID 1898940Notes

Reaction equation

HRID 1898940 reaction equation
ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.[CH:15]([NH:18][C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[CH2:21][OH:22])([CH3:17])[CH3:16]>O1CCOCC1>[CH:15]([NH:18][C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[CH:21]=[O:22])([CH3:17])[CH3:16]

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

After 13.2 g of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) was added by several portions to a solution of 9.6 g of 2-isopropylaminobenzyl alcohol in 200 ml of dioxane, the mixture was stirred for further an hour. The solvent was removed by distillation to concentrate the reaction mixture, and methylene chloride was then 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 obtain 7.6 g of 2-isopropylaminobenzaldehyde.

Workup

  1. customThe solvent was removed by distillation
  2. concentrationto concentrate the reaction mixture, and methylene chloride
  3. additionwas then added
  4. filtrationthereto followed 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-cdd16b9d0d714256a4abf408d41f63eb
Source dataset
uspto-grants-1996_11
Patent number
US05571820

Reaction notes

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