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

HRID 1769459Notes

Reaction equation

HRID 1769459 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-2f6ad18612144d4f83b122569a128f16
Source dataset
uspto-grants-1995_01
Patent number
US05380839

Reaction notes

Loading…