Sodium borohydride → HCID 67198422, compound

HRID 547512Notes

Reaction equation

HRID 547512 reaction equation
C([O:3][C:4]([C:6]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][N:8]([CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:7]=1)=O)C.[BH4-].[Na+]>CO>[N+:11]([C:10]1[C:6]([CH2:4][OH:3])=[N:7][N:8]([CH2:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:9]=1)([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 67196717HCID 67196717, compound

Product 1

HCID 67198422HCID 67198422, compoundYield 69.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

495 mg (1.8 mM) of 4-nitro-1-phenethyl-1H-pyrazole-3-carboxylic acid ethyl ester was dissolved in 5 ml of methyl alcohol, to which 680 mg (18 mM, 13 eq) of sodium borohydride was added dropwise at 0° C., and the resulting mixture was stirred under a nitrogen atmosphere for 1 hour. The solvent was distilled off under reduced pressure, and the resultant was extracted with ethyl acetate and brine. The organic solvent layer was dried over anhydrous sodium sulfate, filtered, and then distilled under reduced pressure. The resulting impure compound was purified by column chromatography (hexane:ethyl acetate=2:1), to obtain 295 mg (66.4%) of the title compound.

Workup

  1. additionwas added dropwise at 0° C.
  2. distillationThe solvent was distilled off under reduced pressure
  3. extractionthe resultant was extracted with ethyl acetate and brine
  4. dry with materialThe organic solvent layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. distillationdistilled under reduced pressure
  7. customThe resulting impure compound was purified by column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-953ef879feef4eeb988aa0ed02b7530b
Source dataset
uspto-grants-2011_05
Patent number
US07939550B2

Reaction notes

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