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

HRID 990978Notes

Reaction equation

HRID 990978 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 Example 7b (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-0bdea34b53e84a23825daca7849a9092
Source dataset
uspto-grants-2002_10
Patent number
US06462036B1

Reaction notes

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