2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 23326436, compound

HRID 1380319Notes

Reaction equation

HRID 1380319 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12](=[O:15])[CH2:13][CH3:14])=[CH:9][CH:10]=2)[CH2:5][CH2:4][C:3]1=[O:16].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1C=CC=CC=1>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12](=[O:15])[CH2:13][CH3:14])=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]1=[O:16]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 13120784HCID 13120784, compound

Product 1

HCID 23326436HCID 23326436, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 1-methyl-2-oxo-6-propionyl-1,2,3,4-tetrahydroquinoline (20 g) and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (20.9 g) in benzene (250 ml) was refluxed for 1 day. The mixture was filtered by suction and evaporated. The residue was chromatographed on silica gel (400 g) with a mixture of benzene and ethyl acetate (1:1) as an eluent. The eluates were concentrated to give an oil of 1-methyl-2-oxo-6-propionyl-1,2-dihydroquinoline (7.72 g).

Workup

  1. filtrationThe mixture was filtered by suction
  2. customevaporated
  3. customThe residue was chromatographed on silica gel (400 g) with a mixture of benzene and ethyl acetate (1:1) as an eluent
  4. concentrationThe eluates were concentrated

Sources & evidence

ORD record
ord-e5a3dc79b9004b87a19c51001a8dcbaf
Source dataset
uspto-grants-1986_04
Patent number
US04581356

Reaction notes

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