Sulfuric Acid → Anthra(1,9-cd)pyrazol-6(2H)-one

HRID 1395120Notes

Reaction equation

HRID 1395120 reaction equation
[C:1]1([NH:17][NH2:18])[C:14]2[C:13](=O)[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6](=[O:16])[C:5]=2[CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)O>O>[CH:10]1[CH:11]=[C:12]2[C:13]3[C:14]4[C:1](=[CH:2][CH:3]=[CH:4][C:5]=4[C:6](=[O:16])[C:7]2=[CH:8][CH:9]=1)[NH:17][N:18]=3

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 178514301HCID 178514301, compound

Product 1

HCID 8515Anthra(1,9-cd)pyrazol-6(2H)-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
40 °C

Procedure

To 55 parts of a moist filter cake containing 24 parts of 1-anthraquinonyl hydrazine (dry weight) obtained by the the procedure described in any one of Examples 1 to 11 are added 150 parts by volume of concentrated sulfuric acid, such that the temperature does not rise above 100° C. (about 1/2 hour). The reaction mixture is then stirred for 2 hours at 100° to 110° C., subsequently cooled to 40° C. and diluted dropwise with 150 parts by volume of water. The suspension is then poured into a mixture of ice and water and filtered. The filter cake is washed neutral with water and dried, affording 22.2 parts of pyrazolanthrone of the formula. ##STR6##

Workup

  1. customobtained by the the procedure
  2. customdoes not rise above 100° C.
  3. custom(about 1/2 hour)
  4. filtrationfiltered
  5. washThe filter cake is washed neutral with water
  6. customdried

Sources & evidence

ORD record
ord-e76eb36fe1e54a81b9f74ed04ed45acd
Source dataset
uspto-grants-1980_05
Patent number
US04202827

Reaction notes

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