Hydrochloric Acid → HCID 178516872, compound

HRID 1591136Notes

Reaction equation

HRID 1591136 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][CH:11]([C:14]3[C:15](=[O:26])[C:16]4[C:21]([C:22](=[O:25])[C:23]=3Cl)=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[OH-:27].[K+].Cl>CO.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:9][CH2:10][CH:11]([C:14]3[C:15](=[O:26])[C:16]4[C:21]([C:22](=[O:25])[C:23]=3[OH:27])=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH2:12][CH2:13]2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 111010701,4-Naphthalenedione, 2-chloro-3-[cis-4-(4-chlorophenyl)cyclohexyl]-

Product 1

HCID 178516872HCID 178516872, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The product of stage (b) was suspended in 10 ml of boiling methanol and 0.55 g of potassium hydroxide in 5.5 ml of water was added dropwise over 15 mins. The mixture was refluxed until a dark red solution formed, (after ca. 6 hrs) when 2 ml of concentrated hydrochloric acid was cautiously added dropwise. The mixture was cooled and filtered, and the solid residue washed thoroughly with water. The water washings were re-acidified and filtered. The combined solid residues (500 mg) mp 200°-209°, were recrystallised from acetonitrile to give the title product as the trans-isomer (300 mg) m.p. 216°-219° C.

Workup

  1. temperatureThe mixture was refluxed until a dark red solution
  2. customformed
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. washthe solid residue washed thoroughly with water
  6. filtrationfiltered
  7. customThe combined solid residues (500 mg) mp 200°-209°, were recrystallised from acetonitrile

Sources & evidence

ORD record
ord-e41521664980424cb503792440ba2c4b
Source dataset
uspto-grants-1993_04
Patent number
US05206268

Reaction notes

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