4-(1-Pyrazolyl)benzonitrile → 4-Pyrazol-1-YL-benzylamine

HRID 625417Notes

Reaction equation

HRID 625417 reaction equation
[N:1]1([C:6]2[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1>[N:1]1([C:6]2[CH:13]=[CH:12][C:9]([CH2:10][NH2:11])=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1

Participants

4

Reactant 2

HCID 120796294-(1-Pyrazolyl)benzonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 27764834-Pyrazol-1-YL-benzylamineYield 0.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Into a 50-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed tetrahydrofuran (15 mL). This was followed by dropwise addition of a 4-(1H-pyrazol-1-yl)benzonitrile (250 mg, 1.48 mmol, 1.00 equiv) in tetrahydrofuran (5 mL) with stirring at 0° C. To this was added LiAlH4 (337 mg, 8.87 mmol, 6.00 equiv). The resulting solution was stirred for 3 h at room temperature. The reaction was then quenched by the addition of NaOH (15%, aq). The resulting solution was extracted with 3×50 mL of dichloromethane and the organic layers were combined, dried over anhydrous sodium sulfate, and concentrated under vacuum. The product was obtained as 0.251 mg of a white crude solid.

Workup

  1. customInto a 50-mL 3-necked round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. stirringThe resulting solution was stirred for 3 h at room temperature
  4. customThe reaction was then quenched by the addition of NaOH (15%, aq)
  5. extractionThe resulting solution was extracted with 3×50 mL of dichloromethane
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-5c60da9387be4ee784cc9cd4b2fd3c29
Source dataset
uspto-grants-2016_04
Patent number
US09301951B2

Reaction notes

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