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

HRID 2372622Notes

Reaction equation

HRID 2372622 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. additionis added
  2. temperatureAfter refluxing
  3. temperaturethe mixture is cooled to 20°-25°
  4. filtrationfiltered

Sources & evidence

ORD record
ord-91f7c3715a1744a6aa97a4c6f86703df
Source dataset
uspto-grants-1992_03
Patent number
US05099019

Reaction notes

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