Hydrazine hydrate (1:1) → 2-(Benzyloxy)-4-hydrazinylbenzonitrile

HRID 505700Notes

Reaction equation

HRID 505700 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[C:15](F)[CH:14]=[CH:13][C:10]=1[C:11]#[N:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[NH2:19][NH2:20]>C(O)C>[CH2:1]([O:8][C:9]1[CH:16]=[C:15]([NH:19][NH2:20])[CH:14]=[CH:13][C:10]=1[C:11]#[N:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 210698282-(Benzyloxy)-4-fluorobenzonitrile

Product 1

HCID 469151942-(Benzyloxy)-4-hydrazinylbenzonitrileYield 75.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-(benzyloxy)-4-fluorobenzonitrile (4.8 g, 21 mmol), in ethanol (80 mL) was treated with hydrazine monohydrate (2.6 g, 2.5 mL, 53 mmol) and heated to reflux for 3 days. The mixture was cooled to room temperature and concentrated. Water was added and the residue was extracted three times with ethyl acetate, dried over magnesium sulfate, filtered and condensed to give 2-(benzyloxy)-4-hydrazinylbenzonitrile (3.8 g, 15.8 mmol, 75% yield) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 4.27 (s, 2H), 5.16 (s, 2H), 6.36 (dd, J=8.73, 1.75 Hz, 1H), 6.61 (d, J=1.61 Hz, 1H), 7.30 (d, J=8.59 Hz, 1H), 7.32-7.51 (m, 5H), 7.78 (s, 1H). ES-MS m/z 240 (M+H)

Workup

  1. temperatureheated
  2. temperatureto reflux for 3 days
  3. concentrationconcentrated
  4. additionWater was added
  5. extractionthe residue was extracted three times with ethyl acetate
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customcondensed

Sources & evidence

ORD record
ord-842e316e3ea1486a8c6f03b78d77c8a1
Source dataset
uspto-grants-2010_08
Patent number
US07781428B2

Reaction notes

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