Methanol → Methyl 4-(1,4-dihydroindeno[1,2-c]pyrazol-3-yl)benzoate

HRID 990977Notes

Reaction equation

HRID 990977 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].[CH3:25]O>C(O)(=O)C>[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]([O:19][CH3:25])=[O:18])=[CH:15][CH:14]=2)=[N:24]1)=[CH:7][CH:6]=[CH:5][CH:4]=3

Participants

5

Reactant 3

HCID 887MethanolHCID 24654Hydrazine hydrate (1:1)HCID 184159234-(1-Oxospiro[indan-2,2'-oxiran]-3'-yl)benzoic acid

Product 1

HCID 18415839Methyl 4-(1,4-dihydroindeno[1,2-c]pyrazol-3-yl)benzoate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidCatalyst

Conditions

Temperature
0 °C

Procedure

A mixture of 4-(1-oxospiro[indan-2,2′-oxiran]-3′-yl)benzoic acid (750 mg), methanol (30 ml) and hydrazine hydrate (0.16 ml) was stirred at ambient temperature whilst glacial acetic acid (6 drops) were added. The mixture was boiled under reflux for 24 hours and then allowed to stand at ambient temperature for 24 hours, then cooled to 0° C. and filtered to give methyl 4-(1,4-dihydroindeno [1,2-c]pyrazol-3-yl)benzoate, m.p. 224-226° C.

Workup

  1. additionwere added
  2. temperatureunder reflux for 24 hours
  3. filtrationfiltered

Sources & evidence

ORD record
ord-928ee3f129e1471dbaa912d962b225d2
Source dataset
uspto-grants-2002_10
Patent number
US06462036B1

Reaction notes

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