Ammonium formate → 2-Hydroxy-4-pyrazol-1-yl-benzonitrile

HRID 1271519Notes

Reaction equation

HRID 1271519 reaction equation
C([O:8][C:9]1[CH:16]=[C:15]([N:17]2[CH:21]=[CH:20][CH:19]=[N:18]2)[CH:14]=[CH:13][C:10]=1[C:11]#[N:12])C1C=CC=CC=1.C([O-])=O.[NH4+]>C1COCC1.[Pd]>[OH:8][C:9]1[CH:16]=[C:15]([N:17]2[CH:21]=[CH:20][CH:19]=[N:18]2)[CH:14]=[CH:13][C:10]=1[C:11]#[N:12]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 184528912-Benzyloxy-4-pyrazol-1-yl-benzonitrile

Product 1

HCID 223926322-Hydroxy-4-pyrazol-1-yl-benzonitrileYield 57.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To 0.395 g of the material from Step B, above, dissolved in 10 mL THF, is added a catalytic amount of 10% Pd/C and excess ammonium formate. The reaction is heated to 50° C. for 45 minutes. Upon cooling, celite is added. The reaction is then gravity filtered and concentrated in vacuo. The residue is redissolved in ethyl acetate and washed with water, brine, dried over sodium sulfate, filtered and concentrated in vacuo to give 0.152 g of the final title compound (57.1%).

Workup

  1. temperatureUpon cooling
  2. additioncelite is added
  3. filtrationgravity filtered
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue is redissolved in ethyl acetate
  6. washwashed with water, brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-112fafd45f344dbfb7153c7b8e378b06
Source dataset
uspto-grants-2007_04
Patent number
US07205313B2

Reaction notes

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