4-Chloro-9,10-dioxo-9,10-dihydroanthracene-1-carboxylic acid → 1-Chloroanthraquinone

HRID 1284148Notes

Reaction equation

HRID 1284148 reaction equation
[Cl:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[C:5](C(O)=O)=[CH:4][CH:3]=1>[Cu-]=O.CN1CCCC1=O>[Cl:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 2355754-Chloro-9,10-dioxo-9,10-dihydroanthracene-1-carboxylic acid

Product 1

HCID 67091-ChloroanthraquinoneYield 90.5%

Reagents, catalysts & solvents 2

HCID 178419072HCID 178419072, compoundCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 25 parts of 4-chloroanthraquinone-1-carboxylic acid, 180 parts of N-methylpyrrolidone, 4 parts of copper(I) oxide and 3 parts of o-phenanthroline hydrochloride is heated for two hours at 150°C. The mixture is poured onto ice and the precipitate formed is suction filtered. After the filter cake has been dissolved in 100 parts of concentrated sulfuric acid and reprecipitated with 300 parts of water, filtered and dried in vacuo at 80°C there are isolated 19 parts (90.5% of theory) of 1-chloroanthraquinone having a melting point of 156° to 158°C.

Workup

  1. additionThe mixture is poured onto ice
  2. customthe precipitate formed
  3. filtrationfiltered
  4. dissolutionAfter the filter cake has been dissolved in 100 parts of concentrated sulfuric acid
  5. customreprecipitated with 300 parts of water
  6. filtrationfiltered
  7. customdried in vacuo at 80°C

Sources & evidence

ORD record
ord-ea878a583d8f4a88982a42476b2499df
Source dataset
uspto-grants-1976_08
Patent number
US03978096

Reaction notes

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