Sulfuric Acid → HCID 22567058, compound

HRID 25455Notes

Reaction equation

HRID 25455 reaction equation
[N+:1]([O-:4])([O-])=[O:2].[K+].[CH3:6][C:7]1[CH:15]=[C:14]2[C:10]([C:11]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:12][NH:13]2)=[CH:9][CH:8]=1.S(=O)(=O)(O)O>>[CH3:6][C:7]1[CH:15]=[C:14]2[C:10]([C:11]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[N:12][NH:13]2)=[CH:9][C:8]=1[N+:1]([O-:4])=[O:2]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 24434Potassium NitrateHCID 22567225HCID 22567225, compound

Product 1

HCID 22567058HCID 22567058, compoundYield 47.3%

Conditions

Temperature
0 °C

Procedure

6-Methyl-5-nitro-3-phenyl-1H-indazole can be obtained in the following way: 0.43 g of potassium nitrate is added over 5 minutes to a solution, cooled to a temperature in the region of 0° C., of 0.8 g of 6-methyl-3-phenyl-1H-indazole in 8 ml of an aqueous 98% sulfuric acid solution. The reaction mixture is stirred at a temperature in the region of 0° C. for 5 minutes and is then heated at a temperature in the region of 35-40° C. for 10 minutes and again cooled to a temperature in the region of 0° C. and stirred for 1 hour. The mixture is then poured into 50 g of ice, stirred at a temperature in the region of 0° C. for 1 hour, then filtered through sintered glass. The solid obtained is washed with 3 times 30 ml of water and partially dried and is then redissolved in 100 ml of ethyl acetate and the mixture is dried over magnesium sulfate, filtered and then concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. The residue thus obtained is purified by chromatography on a silica column (particle size 40-63 μm), eluting successively with cyclohexane/ethyl acetate (90/10; 80/20 by volume) mixtures. The fractions containing the expected product are pooled and concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. 0.46 g of 6-methyl-5-nitro-3-phenyl-1H-indazole is thus obtained in the form of a yellow crystalline solid melting at 164° C.

Workup

  1. temperatureis then heated at a temperature in the region of 35-40° C. for 10 minutes
  2. temperatureagain cooled to a temperature in the region of 0° C.
  3. stirringstirred for 1 hour
  4. stirringstirred at a temperature in the region of 0° C. for 1 hour
  5. filtrationfiltered through sintered glass
  6. customThe solid obtained
  7. washis washed with 3 times 30 ml of water
  8. custompartially dried
  9. dissolutionis then redissolved in 100 ml of ethyl acetate
  10. dry with materialthe mixture is dried over magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C
  13. customThe residue thus obtained
  14. customis purified by chromatography on a silica column (particle size 40-63 μm)
  15. washeluting successively with cyclohexane/ethyl acetate (90/10; 80/20 by volume) mixtures
  16. additionThe fractions containing the expected product
  17. concentrationconcentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C

Sources & evidence

ORD record
ord-142c99f5ed32453cb02e115b8fc18c0c
Source dataset
uspto-grants-2005_02
Patent number
US06858638B2

Reaction notes

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