Methanol → HCID 178497612, compound

HRID 1605017Notes

Reaction equation

HRID 1605017 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:21]=[C:12]3[C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=4[C:19](=[O:20])[N:11]3[N:10]=2)=[CH:5][CH:4]=1.[Na].[CH3:23][OH:24]>>[C:19]([C:18]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:12]1[CH:21]=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[NH:10][N:11]=1)([O:24][CH3:23])=[O:20]

Participants

4

Reactant 3

HCID 887MethanolHCID 1397657HCID 1397657, compoundHCID 5360545Sodium

Product 1

HCID 178497612HCID 178497612, compound

Procedure

A mixture of 2-(4-methoxyphenyl)pyrazolo[5,1-a]isoindol-8-one (100 mg), methanol(10 ml), and sodium (0.1 g), was stirred overnight at 25°. Evaporation of the methanol left 120 mg (96%) of colorless gum which was the ester 3-(2-carbomethoxyphenyl)-5-(4-methoxyphenyl)pyrazole. The crude ester was dissolved in benzene and stirred overnight with 2 g of Florisil. Filtration and evaporation of the benzene solution, followed by recrystallization from hexane-ethyl acetate (1:1), gave 3-(2-carbomethoxyphenyl)-5-(4-methoxyphenyl)pyrazole, mp 92°-93°.

Workup

  1. customEvaporation of the methanol
  2. waitleft 120 mg (96%) of colorless gum which
  3. dissolutionThe crude ester was dissolved in benzene
  4. stirringstirred overnight with 2 g of Florisil
  5. filtrationFiltration and evaporation of the benzene solution
  6. customfollowed by recrystallization from hexane-ethyl acetate (1:1)

Sources & evidence

ORD record
ord-d7290ca25a4f42f3af690d98154ea199
Source dataset
uspto-grants-1976_04
Patent number
US03948937

Reaction notes

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