2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 21449334, compound

HRID 597044Notes

Reaction equation

HRID 597044 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:12]3[C:20]4[C:15](=[CH:16][C:17]([O:21][CH3:22])=[CH:18][CH:19]=4)[CH:14]([CH2:23][C:24]([O:26][CH3:27])=[O:25])[CH:13]3[CH3:28])=[CH:7][N:8]=[N:9]2)=[CH:4][CH:3]=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>COCCOC>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:12]3[C:20]4[C:15](=[CH:16][C:17]([O:21][CH3:22])=[CH:18][CH:19]=4)[C:14]([CH2:23][C:24]([O:26][CH3:27])=[O:25])=[C:13]3[CH3:28])=[CH:7][N:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 54524512HCID 54524512, compound

Product 1

HCID 21449334HCID 21449334, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

A solution of methyl 1-(7-chlorocinnolin-4-yl)-5-methoxy-2-methylindolin-3-ylacetate (7.9g.) in dry 1,2-dimethoxyethane [80ml.; dried over sodium alumino-silicate (molecular sieve type 4A; obtainable from BDH Chemicals Ltd., Poole, England)] was mixed with a solution of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (4.5g.) in dry 1,2-dimethoxyethane (30ml.). The solution was heated under reflux for 20 minutes and then evaporated in vacuo. The residue was extracted with chloroform (5 × 50ml.). Evaporation of the extracts gave an oil, which was purified by chromatography on silica gel (350g.), using ether as eluant, to give methyl 1-(7-chlorocinnolin-4-yl)-5-methoxy-2-methylindol-3-ylacetate as a red syrup, homogeneous by thin layer chromatography (ether: silica gel) [hereinafter referred to as system C], and having a satisfactory NMR spectrum (5-OCH3, τ6.13).

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux for 20 minutes
  3. customevaporated in vacuo
  4. extractionThe residue was extracted with chloroform (5 × 50ml.)
  5. customEvaporation of the extracts
  6. customgave an oil, which
  7. customwas purified by chromatography on silica gel (350g.)

Sources & evidence

ORD record
ord-e945406c019641479a5334fb8be36903
Source dataset
uspto-grants-1977_03
Patent number
US04012513

Reaction notes

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