2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 6-Phenylindolo[1,7-ab][1,5]benzodiazepine

HRID 2052706Notes

Reaction equation

HRID 2052706 reaction equation
[C:1]1([C:7]2[C:8]3[CH:23]=[CH:22][CH:21]=[C:20]4[C:9]=3[N:10]([CH2:18][CH2:19]4)[C:11]3[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=3[N:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1(C)C(C)=CC=CC=1>[C:1]1([C:7]2[C:8]3[CH:23]=[CH:22][CH:21]=[C:20]4[C:9]=3[N:10]([CH:18]=[CH:19]4)[C:11]3[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=3[N:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 125191401,2-Dihydro-6-phenylindolo[1,7-ab][1,5]benzodiazepine

Product 1

HCID 125191586-Phenylindolo[1,7-ab][1,5]benzodiazepine

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A stirred solution, under N2, of 8.7 g of 1,2-dihydro-6-phenylindolo[1,7-ab][1,5]benzodiazepine in 125 ml of xylene is heated to 100° C. when 7.34 g of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) is added in one portion. The mixture is brought to reflux and kept there for 3.0 hours. After cooling to room temperature, the liquid is filtered and the residue remaining in the flask is rinsed with xylene. The xylene filtrate is concentrated to an oil. This oil is dissolved in ethanol, and the solution is allowed to cool at 0° C. The crystals so obtained are filtered, washed with a little ethanol, then dried to yield 6-phenylindolo[1,7-ab][1,5]benzodiazepine, m.p. 128°-136° C.

Workup

  1. additionis added in one portion
  2. temperatureto reflux
  3. filtrationthe liquid is filtered
  4. washis rinsed with xylene
  5. concentrationThe xylene filtrate is concentrated to an oil
  6. dissolutionThis oil is dissolved in ethanol
  7. temperatureto cool at 0° C
  8. customThe crystals so obtained
  9. filtrationare filtered
  10. washwashed with a little ethanol
  11. customdried

Sources & evidence

ORD record
ord-3fc7c4b5aee740d0899270c9329ccbd7
Source dataset
uspto-grants-1980_01
Patent number
US04186199

Reaction notes

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