Hydrochloric Acid → 3-Amino-5-nitrobenzonitrile

HRID 889440Notes

Reaction equation

HRID 889440 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([N+:12]([O-])=O)[CH:11]=1)[C:7]#[N:8])([O-:3])=[O:2].Cl>CO.[Fe]>[NH2:12][C:10]1[CH:9]=[C:6]([CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:11]=1)[C:7]#[N:8]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 20062Benzonitrile, 3,5-dinitro-

Product 1

HCID 112289743-Amino-5-nitrobenzonitrileYield 61%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

To a suspension of 3,5-dinitrobenzonitrile (4.5 g, 23.30 mmol) in MeOH (100 mL) was added concentrated HCl (15 mL), followed by iron powder (3.90 g, 69.9 mmol). The mixture was stirred at room temperature for 30 min. and then concentrated. The residue was treated with water and the resulting solid product was collected by filtration to give Intermediate 71A (2.3 g, 61%). HPLC: Rt=1.245 min. (CHROMOLITH® column 4.6×50 mm eluting with 10-90% aqueous methanol over 4 min. containing 0.1% TFA, 4 mL/min., monitoring at 220 nm). 1H NMR (500 MHz, DMSO-d6) δ ppm 7.68 (1H, s), 7.64 (1H, s), 7.24 (1H, s), 6.33 (2H, s).

Workup

  1. concentrationconcentrated
  2. additionThe residue was treated with water
  3. filtrationthe resulting solid product was collected by filtration

Sources & evidence

ORD record
ord-9e89093310f64b6a97c8309302f6df43
Source dataset
uspto-grants-2012_08
Patent number
US08252795B2

Reaction notes

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