2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 54339148, compound

HRID 326489Notes

Reaction equation

HRID 326489 reaction equation
[CH3:1][CH:2]1[C@H:19]([C:20]([CH3:22])=[O:21])[C@:18]2([CH3:23])[C@H:4]([C@H:5]3[C@H:15]([CH2:16][CH2:17]2)[C@:14]2([CH3:24])[C:8](=[CH:9][C:10]([CH2:12][CH2:13]2)=[O:11])[CH2:7][CH2:6]3)[CH2:3]1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C1C=CC=CC=1>[CH3:1][C@@H:2]1[CH2:3][C@@H:4]2[C@:18]([CH3:23])([CH2:17][CH2:16][C@H:15]3[C@H:5]2[CH2:6][CH2:7][C:8]2[C@:14]3([CH3:24])[CH:13]=[CH:12][C:10](=[O:11])[CH:9]=2)[C@H:19]1[C:20](=[O:21])[CH3:22]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinone2×HCID 13487416-Methylprogesterone

Product 1

HCID 54339148HCID 54339148, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 16α-methylprogesterone (792 mg), DDQ (575 mg) and benzene are heated at reflux for 28 hr, after 20 hr additional DDQ (70 mg) is added. After refluxing, the mixture is cooled to 20°-25°, filtered followed by basic workup (ether-potassium carbonate-magnesium sulfate) to give 16α-methylpregna-1,4-diene-3,20-dione.

Workup

  1. temperatureare heated
  2. additionis added
  3. temperatureAfter refluxing
  4. temperaturethe mixture is cooled to 20°-25°
  5. filtrationfiltered

Sources & evidence

ORD record
ord-84e85e9de80045c1b8a9e11396d1d066
Source dataset
uspto-grants-1993_12
Patent number
US05268477

Reaction notes

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