Chloranil → HCID 21449365, compound

HRID 597043Notes

Reaction equation

HRID 597043 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][CH2:27][CH3:28])=[O:25])[CH:13]3[CH3:29])=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.ClC1C(=O)C(Cl)=C(Cl)C(=O)C=1Cl>C1(C)C(C)=CC=CC=1>[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][CH2:27][CH3:28])=[O:25])=[C:13]3[CH3:29])=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 8371ChloranilHCID 53796277HCID 53796277, compound

Product 1

HCID 21449365HCID 21449365, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of ethyl 1-(7-chloroquinol-4-yl)-5-methoxy-2-methylindolin-3-ylacetate (7.0g.) and 2,3,5,6-tetrachloro-1,4-benzoquinone (5.6g.) in dry xylene (50ml.) was heated under reflux for 1.5 hours. The mixture was then cooled and filtered. The filtrate was washed successively with cold 2N-sodium hydroxide solution (2 × 30ml.) and water (2 × 50ml.). The organic layer was dried (MgSO4) and evaporated in vacuo to dryness, and the residue (dissolved in the minimum volume of diethyl ether) was adsorbed on a column of chromatographic silica gel (column dimensions: 15 × 3.5cm.). The column was eluted with a 1:3 v/v mixture of diethyl ether and petroleum ether (b.p. 40°-60° C.), and the eluate was evaporated in vacuo to give ethyl 1-(7-chloroquinol-4-yl)-5-methoxy-2-methylindol-3-ylacetate as a yellow oil, NMR: -OCH3, τ6.12.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1.5 hours
  3. temperatureThe mixture was then cooled
  4. filtrationfiltered
  5. washThe filtrate was washed successively with cold 2N-sodium hydroxide solution (2 × 30ml.) and water (2 × 50ml.)
  6. dry with materialThe organic layer was dried (MgSO4)
  7. customevaporated in vacuo to dryness
  8. dissolutionthe residue (dissolved in the minimum volume of diethyl ether)
  9. washThe column was eluted with a 1:3 v/v mixture of diethyl ether and petroleum ether (b.p. 40°-60° C.)
  10. customthe eluate was evaporated in vacuo

Sources & evidence

ORD record
ord-56389dbc63a84fad8efdfb8364371d8d
Source dataset
uspto-grants-1977_03
Patent number
US04012513

Reaction notes

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