2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 19095343, compound

HRID 486585Notes

Reaction equation

HRID 486585 reaction equation
[CH3:1][CH:2]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[C:8]2[N:7]([CH2:15][CH2:16][NH:17][C:18](=[O:20])[CH3:19])[CH:6]=[CH:5][C:4]=2[CH2:3]1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=13)[N:7]([CH2:15][CH2:16][NH:17][C:18](=[O:20])[CH3:19])[CH:6]=[CH:5]2

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinone2×HCID 19095277HCID 19095277, compound

Product 1

HCID 19095343HCID 19095343, compoundYield 6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

N-[2-(4,5-Dihydro-5-methyl-1H-benzo[g]indol-1-yl)ethyl]acetamide (5.0 g) was suspended in 80 ml of toluene under argon, treated with 4.7 g of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and stirred at 80° C. for 4 hours. A further 1.0 g of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone was added and the mixture was stirred at 80° C. for a further 1 hour. The solution was cooled and filtered over 60 g of aluminium oxide (neutral, III) with ethyl acetate as the eluent. The filtrate was concentrated and yielded 0.3 g (6%) of N-[2-(5-methyl-1H-benzo[g]indol-1-yl)ethyl]acetamide as an amorphous, yellow solid which was processed without further purification.

Workup

  1. stirringthe mixture was stirred at 80° C. for a further 1 hour
  2. temperatureThe solution was cooled
  3. filtrationfiltered over 60 g of aluminium oxide (neutral, III) with ethyl acetate as the eluent
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-0d159688ef854a2ab788930b56021255
Source dataset
uspto-grants-1994_03
Patent number
US05292732

Reaction notes

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