p-Toluenesulfonic acid → HCID 135512470, compound

HRID 990990Notes

Reaction equation

HRID 990990 reaction equation
O=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C:3]1=[CH:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1.C1(C)C=CC(S([NH:28][NH2:29])(=O)=O)=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[NH:28]1[C:2]2[C:10]3[C:5]([CH2:4][C:3]=2[C:11]([C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)=[N:29]1)=[CH:6][CH:7]=[CH:8][CH:9]=3

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 15303P-ToluenesulfonylhydrazideHCID 53775483HCID 53775483, compound

Product 1

HCID 135512470HCID 135512470, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-(1-oxoindan-2-ylidenemethyl)phenol (1.67 g, Chem. Ber. 1901, 34, 413), p-toluenesulphonyl hydrazine (1.95 g), p-toluenesulphonic acid (0.27 g) and ethanol (15 ml) was boiled under reflux for 72 hours. The solvent was removed under reduced pressure and the residue was purified by flash column chromatography on silica using petroleum ether, b.p. 60-80° C./ethyl acetate (1:1) as the mobile phase. Appropriate fractions were collected, combined and evaporated to give a residue which was triturated with petroleum ether, b.p. 60-80° C., to give a solid which was crystallized from ethanol to give 4-(1,4-dihydroindeno[1,2-c]pyrazol-3-yl)phenol, m.p. 266-268° C.

Workup

  1. temperatureunder reflux for 72 hours
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was purified by flash column chromatography on silica
  4. customAppropriate fractions were collected
  5. customevaporated
  6. customto give a residue which
  7. customwas triturated with petroleum ether, b.p. 60-80° C.
  8. customto give a solid which
  9. customwas crystallized from ethanol

Sources & evidence

ORD record
ord-6f5fb2ed6ffb420f828104a108e24f6b
Source dataset
uspto-grants-2002_10
Patent number
US06462036B1

Reaction notes

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