2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 19095280, compound

HRID 486550Notes

Reaction equation

HRID 486550 reaction equation
[N:1]1([CH2:14][CH2:15][NH:16][C:17](=[O:19])[CH3:18])[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[CH2:6][CH2:5][C:4]=2[CH:3]=[CH:2]1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1(C)C=CC=CC=1>[N:1]1([CH2:14][CH2:15][NH:16][C:17](=[O:19])[CH3:18])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]3=2)[CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinone2×HCID 19095320HCID 19095320, compound

Product 1

HCID 19095280HCID 19095280, compoundYield 30.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

N-[2-(4,5-Dihydro-1H-benzo[g]indol-1-yl)ethyl]acetamide (4.0 g) was dissolved in 50 ml of toluene under argon and treated with 3.8 g of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ). The reaction mixture was stirred at 80° C. for 2 hours, a further 0.4 g of DDQ was then added and the mixture was stirred at 80° C. for a further 2 hours. The separated precipitate was filtered off at room temperature and the filtrate was freed from solvent. The crude product, 1.5 g of dark brown solid, was chromatographed on 60 g of neutral aluminium oxide with ethyl acetate as the eluent. There were obtained 1.2 g (30%) of N-[2-(1H-benzo[g]indol-1-yl)ethyl]acet-amide which was processed without further purification.

Workup

  1. stirringthe mixture was stirred at 80° C. for a further 2 hours
  2. filtrationThe separated precipitate was filtered off at room temperature
  3. customThe crude product, 1.5 g of dark brown solid, was chromatographed on 60 g of neutral aluminium oxide with ethyl acetate as the eluent

Sources & evidence

ORD record
ord-4dae246a17d041a2b078c6a27aba83b5
Source dataset
uspto-grants-1994_03
Patent number
US05292732

Reaction notes

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