Hydrochloric Acid → HCID 178516894, compound

HRID 1754228Notes

Reaction equation

HRID 1754228 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.C[OH:28].[OH-].[K+].Cl>O>[CH:18]1[CH:19]=[CH:20][C:21]2[C:22]([C:23]([OH:28])=[C:14]([C@@H:11]3[CH2:10][CH2:9][C@@H:8]([C:5]4[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=4)[CH2:13][CH2:12]3)[C:15](=[O:26])[C:16]=2[CH:17]=1)=[O:25]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14797Potassium HydroxideHCID 111010701,4-Naphthalenedione, 2-chloro-3-[cis-4-(4-chlorophenyl)cyclohexyl]-

Product 1

HCID 178516894HCID 178516894, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
27.5 °C

Procedure

2-[4-(4-Chlorophenyl)cyclohexyl-3-chloro-1,4-naphthoquinone (20 gm) was added to methanol (400 ml) at 25-30° C., the contents were heated to reflux and then potassium hydroxide solution (20 gm) in water (200 ml) was slowly added for 30 minutes at reflux. The reaction mass was stirred for 6 hours at reflux, to the resulting mass added hydrochloric acid (72 ml) slowly for 15 to 20 minutes at reflux and then cooled to 25-30° C. The resulting mass was further cooled to 0° C. and then stirred for 1 hour at 0-5° C. The solid was filtered, washed with water and then dried at 50-60° C. to give 18.1 gm of atovaquone.

Workup

  1. temperaturethe contents were heated
  2. temperatureto reflux
  3. temperatureat reflux
  4. temperatureat reflux, to the resulting mass
  5. temperatureat reflux
  6. temperatureThe resulting mass was further cooled to 0° C.
  7. stirringstirred for 1 hour at 0-5° C
  8. filtrationThe solid was filtered
  9. washwashed with water
  10. customdried at 50-60° C.

Sources & evidence

ORD record
ord-b52231961bc14824ac1835fdde37ef5d
Source dataset
uspto-grants-2015_10
Patent number
US09169232B2

Reaction notes

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