4-Aminobenzonitrile → 4-Hydrazinobenzonitrile

HRID 59254Notes

Reaction equation

HRID 59254 reaction equation
[C:1]([C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1)#[N:2].[N:10]([O-])=O.[Na+]>Cl>[NH:7]([C:6]1[CH:8]=[CH:9][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1)[NH2:10]

Participants

4

Reactant 2

HCID 133964-AminobenzonitrileHCID 23668193Sodium Nitrite

Product 1

HCID 5837844-HydrazinobenzonitrileYield 71,006.398%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

Conditions

Temperature
5 °C

Procedure

To a cold solution of 4-cyanoaniline (6.0 g, 0.050 mol) in conc. HCl was added aq. solution of sodium nitrite (3.85 g, 0.055 mmol) at −15° C. The reaction mass was stirred at 0-10° C. for 15 minutes and filtered off to remove insolubles. The filtrate was added to stannous chloride in conc. HCl (24.0 g, 0.166 mmol). The reaction mass was stirred at −15° C. for 30 minutes. The reaction mass was filtered to afford 5.2 g of desired product. 1H NMR (300 MHz, DMSO d6): δ 7.04 (d, 2H), 7.70 (d, 2H), 9.17 (br s, 1H), 10.66 (br s, 2H).

Workup

  1. filtrationfiltered off
  2. customto remove insolubles
  3. stirringThe reaction mass was stirred at −15° C. for 30 minutes
  4. filtrationThe reaction mass was filtered

Sources & evidence

ORD record
ord-4053ed7b915e4999932e1988aec78d86
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

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