Hydrazine hydrate (1:1) → 4-(Aminomethyl)benzonitrile

HRID 485273Notes

Reaction equation

HRID 485273 reaction equation
C1(=O)[N:5]([CH2:6][C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=2)C(=O)C2=CC=CC=C12.O.NN>CO>[NH2:12][CH2:11][C:10]1[CH:13]=[CH:14][C:7]([C:6]#[N:5])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 854235HCID 854235, compound

Product 1

HCID 826084-(Aminomethyl)benzonitrileYield 90.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Next, 26.0 g (99 mmols) of 4-phthalimidomethylbenzonitrile prepared in the same manner as above was admixed with 6.32 ml (0.129 mol) of hydrazine hydrate and 300 ml of methanol. The mixture was refluxed for 1 hour, cooled to room temperature and concentrated. The residue was dissolved in 300 ml of 1 mol dm-3NaOH, followed by extraction with ether. The ethereal layer was washed with saturated aqueous solution of sodium chloride, dryed over MgSO4 and concentrated, affording 11.8 g (yield 90%) of 4-aminomethylbenzonitrile.

Workup

  1. temperatureThe mixture was refluxed for 1 hour
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in 300 ml of 1 mol dm-3NaOH
  4. extractionfollowed by extraction with ether
  5. washThe ethereal layer was washed with saturated aqueous solution of sodium chloride
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9d034a658eb4464abd96bf4d27c90218
Source dataset
uspto-grants-1985_08
Patent number
US04536391

Reaction notes

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