2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 54288891, compound

HRID 728551Notes

Reaction equation

HRID 728551 reaction equation
[CH2:1]1[CH2:13][CH2:12][CH:11]2[CH2:14][CH2:15][CH2:16][N:9]3[C:10]2=[C:2]1[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:8]=13.ClC1C(=O)C(C#N)=C(C#N)C(=[O:25])C=1Cl>O1CCCC1.O>[C:1]1(=[O:25])[CH2:13][CH2:12][CH:11]2[CH2:14][CH2:15][CH2:16][N:9]3[C:10]2=[C:2]1[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:8]=13

Participants

5

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 12582037HCID 12582037, compound

Product 1

HCID 54288891HCID 54288891, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

7.2 g (0.034 mol) of 2,3,3a,4,5,6-hexahydro-1H-pyrido[3,2,1-jk]carbazole prepared according to A. S. Baily et al. J. C. S. Perkin I (1980) 97, were dissolved in 300 ml of tetrahydrofuran. The mixture was diluted with 30 ml of water and cooled to 0° C. A solution of 17.0 g (0.075 mol) of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone in 150 ml of tetrahydrofuran was added dropwise in 10 minutes while stirring thoroughly at a reaction temperature between 0° and 5° C. The reaction mixture was stirred for 1 hour and evaporated in vacuum. The residue was extracted with methylene chloride. The methylene chloride solution was washed with 200 ml of 0.5N sodium hydroxide solution and evaporated in vacuum. The residue was chromatographed over 500 g of silicagel using ethyl acetate as an eluent. After evaporating the good fraction, the desired ketone was obtained in a yield of 4.6 g (60%) having a melting-point of 172°-173° C.

Workup

  1. stirringThe reaction mixture was stirred for 1 hour
  2. customevaporated in vacuum
  3. extractionThe residue was extracted with methylene chloride
  4. washThe methylene chloride solution was washed with 200 ml of 0.5N sodium hydroxide solution
  5. customevaporated in vacuum
  6. customThe residue was chromatographed over 500 g of silicagel
  7. customAfter evaporating the good fraction

Sources & evidence

ORD record
ord-b6ca8e4e464f45b5ae355b5785b88f33
Source dataset
uspto-grants-1991_09
Patent number
US05049563

Reaction notes

Loading…