Methanol → HCID 135600008, compound

HRID 1175811Notes

Reaction equation

HRID 1175811 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:9]2[CH:13]=[C:12]([C:14](O)=[O:15])[C:11]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N+:23]([O-])=O)=[N:10]2)[CH:6]=[CH:7][CH:8]=1.CO>[Pd].O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:9]2[CH:13]=[C:12]3[C:14](=[O:15])[NH:23][C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=4[C:11]3=[N:10]2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 23153898HCID 23153898, compound

Product 1

HCID 135600008HCID 135600008, compoundYield 82.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 1-(3-methoxyphenyl)-3-(2-nitrophenyl)-1H-pyrazole-4-carboxylic acid (500 mg), 10% palladium/active carbon (50% water, 50 mg), tetrahydrofuran (30 ml) and methanol (50 ml) was stirred under hydrogen atmosphere, at room temperature for one night. To the reaction mixture was added tetrahydrofuran to dissolve the precipitated solid and the reaction mixture was filtered. The filtrate was concentrated under reduced pressure. To the residue was added ethanol-ethyl acetate, and the solid was collected by filtration. The solid was washed with ethyl acetate and dried to obtain the target compound (353 mg).

Workup

  1. dissolutionto dissolve the precipitated solid
  2. filtrationthe reaction mixture was filtered
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. additionTo the residue was added ethanol-ethyl acetate
  5. filtrationthe solid was collected by filtration
  6. washThe solid was washed with ethyl acetate
  7. customdried

Sources & evidence

ORD record
ord-e88f810638c94694aec182b95c3730e4
Source dataset
uspto-grants-2010_11
Patent number
US07842701B2

Reaction notes

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