Dimethyl 4-benzyloxy-1-(2-nitrophenyl)-1H-pyrazole-3,5-dicarboxylate → HCID 68953398, compound

HRID 1453877Notes

Reaction equation

HRID 1453877 reaction equation
C([O:8][C:9]1[C:10]([C:27]([O:29][CH3:30])=[O:28])=[N:11][N:12]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[N+:24]([O-])=O)[C:13]=1[C:14](OC)=[O:15])C1C=CC=CC=1>CO.[Pd]>[OH:8][C:9]1[C:10]([C:27]([O:29][CH3:30])=[O:28])=[N:11][N:12]2[C:18]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[NH:24][C:14](=[O:15])[C:13]=12

Participants

4

Reactant 1

HCID 57528497Dimethyl 4-benzyloxy-1-(2-nitrophenyl)-1H-pyrazole-3,5-dicarboxylate

Product 1

HCID 68953398HCID 68953398, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of dimethyl 4-benzyloxy-1-(2-nitrophenyl)-1H-pyrazole-3,5-dicarboxylate (2.0 g, 4.85 mmol) in MeOH (100 mL) was added palladium on carbon (200 mg). The mixture was then stirred and purged with hydrogen gas. The mixture was stirred at ambient temperature under 1 atmosphere of hydrogen gas for 72 hours. The mixture was filtered through celite and the filter cake was washed with MeOH. The filtrate solvent was removed under reduced pressure. Trituration of the residue in a small volume of MeOH gave the product as a white solid. 1H NMR (400 MHz, d6-DMSO) δ 11.65 (s, 1H), 9.74 (s, 1H), 8.07 (d, J=8.2 Hz, 1H), 7.41 (t, J=7.9 Hz, 1H), 7.25-7.34 (m, 2H), 3.88 (s, 3H); ES MS (M+1)=260.

Workup

  1. custompurged with hydrogen gas
  2. stirringThe mixture was stirred at ambient temperature under 1 atmosphere of hydrogen gas for 72 hours
  3. filtrationThe mixture was filtered through celite
  4. washthe filter cake was washed with MeOH
  5. customThe filtrate solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-8f62176fcbf3415ba22e63e21e392e26
Source dataset
uspto-grants-2009_01
Patent number
US07476666B2

Reaction notes

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