3-(5-Nitrofuran-2-yl)-1-phenyl-1H-pyrazole-4-carboxylic acid → [3-(5-Nitrofuran-2-yl)-1-phenyl-1H-pyrazol-4-yl]methanol

HRID 839246Notes

Reaction equation

HRID 839246 reaction equation
[N+:1]([C:4]1[O:8][C:7]([C:9]2[C:13]([C:14](O)=[O:15])=[CH:12][N:11]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:10]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]>O1CCOCC1>[OH:15][CH2:14][C:13]1[C:9]([C:7]2[O:8][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)=[N:10][N:11]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:12]=1

Participants

3

Reactant 1

HCID 203259643-(5-Nitrofuran-2-yl)-1-phenyl-1H-pyrazole-4-carboxylic acid

Product 1

HCID 20326211[3-(5-Nitrofuran-2-yl)-1-phenyl-1H-pyrazol-4-yl]methanol

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To obtain the starting material, stir 1.2 ml of a 70% solution of sodium dihydro-bis-(2-methoxyethoxy)aluminate together with 0.6 g of 3-(5-nitro-2-furyl)-1-phenylpyrazole-4-carboxylic acid and 15 ml of dioxane at 70° C for 1.5 hours. Then add thereto 0.16 ml of 15% caustic soda and 0.5 ml of water at room temperature before filtering the thus-prepared product while warm. Extract the filtered precipitate with dioxane, concentrate the combined dioxane solutions and crystallize from ethanol to obtain 4-hydroxymethyl-3-(5-nitro-2-furyl)-1-phenylpyrazole [m.p. 148° to 149° C].

Workup

  1. customTo obtain the starting material
  2. additionThen add
  3. filtration0.16 ml of 15% caustic soda and 0.5 ml of water at room temperature before filtering the thus-prepared product
  4. temperaturewhile warm
  5. extractionExtract the filtered precipitate with dioxane
  6. concentrationconcentrate the combined dioxane solutions
  7. customcrystallize from ethanol

Sources & evidence

ORD record
ord-aa0cd1dee3314f3a9448f41f60553dc9
Source dataset
uspto-grants-1978_06
Patent number
US04093812

Reaction notes

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