Hydrazine hydrate (1:1) → 4-(1,4-Dihydroindeno[1,2-c]pyrazol-3-yl)benzoic acid

HRID 378847Notes

Reaction equation

HRID 378847 reaction equation
O=[C:2]1[C:10]2([CH:12]([C:13]3[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=3)O2)[CH2:9][C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.O.[NH2:23][NH2:24]>C(O)(=O)C.CO>[NH:23]1[C:2]2[C:3]3[C:8]([CH2:9][C:10]=2[C:12]([C:13]2[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=2)=[N:24]1)=[CH:7][CH:6]=[CH:5][CH:4]=3

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 184159234-(1-Oxospiro[indan-2,2'-oxiran]-3'-yl)benzoic acid

Product 1

HCID 184158474-(1,4-Dihydroindeno[1,2-c]pyrazol-3-yl)benzoic acid

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

4-(1-Oxospiro[indan-2,2′-oxiran]-3′-yl)benzoic acid from part b) (780 mg), methanol (50 ml), hydrazine hydrate (0.18 ml) and glacial acetic acid (6 drops) were boiled under reflux for 24 hours. The mixture was cooled in ice and filtered to give 4-(1,4-dihydroindeno[1,2-c]pyrazol-3-yl)benzoic acid, m.p. >320° C.

Workup

  1. temperatureunder reflux for 24 hours
  2. temperatureThe mixture was cooled in ice
  3. filtrationfiltered

Sources & evidence

ORD record
ord-b0af8d13f0ad480c9842913eda358c2e
Source dataset
uspto-grants-2001_10
Patent number
US06297238B1

Reaction notes

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