2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 19808754, compound

HRID 373994Notes

Reaction equation

HRID 373994 reaction equation
[Cl:1][C:2]1[C:14]2[NH:13][C:12]3[CH2:11][CH2:10][CH2:9][CH2:8][C:7]=3[C:6]=2[C:5]([C:15]([O:17][CH3:18])=[O:16])=[C:4]([C:19]([O:21][CH3:22])=[O:20])[CH:3]=1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>ClC1C=CC=CC=1Cl>[Cl:1][C:2]1[C:14]2[NH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[C:5]([C:15]([O:17][CH3:18])=[O:16])=[C:4]([C:19]([O:21][CH3:22])=[O:20])[CH:3]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 19808730HCID 19808730, compound

Product 1

HCID 19808754HCID 19808754, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

To 5 ml of o-dichlorobenzene were added 50 mg of dimethyl 1-chloro-5,6,7,8-tetrahydrocarbazole-3,4-dicarboxylate and 80 mg of DDQ. The mixture was refluxed for 1 hour. The solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography (eluant: toluene/ethyl acetate=1/0 to 20/1) to obtain 40 mg (yield: 81%) of dimethyl 1-chlorocarbazole-3,4-dicarboxylate as colorless crystals.

Workup

  1. temperatureThe mixture was refluxed for 1 hour
  2. customThe solvent was removed by distillation under reduced pressure
  3. customThe residue was purified by column chromatography (eluant: toluene/ethyl acetate=1/0 to 20/1)

Sources & evidence

ORD record
ord-4c5c2af1f6e04a018cb46a391a66057b
Source dataset
uspto-grants-1992_11
Patent number
US05166204

Reaction notes

Loading…