Hydrochloric Acid → 5-Amino-2-chlorobenzonitrile

HRID 1500060Notes

Reaction equation

HRID 1500060 reaction equation
Cl.[Cl:2][C:3]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][C:4]=1[C:5]#[N:6].O.O.Cl[Sn]Cl.[OH-].[Na+]>C(O)(C)C>[NH2:11][C:8]1[CH:9]=[CH:10][C:3]([Cl:2])=[C:4]([CH:7]=1)[C:5]#[N:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 855042-Chloro-5-nitrobenzonitrile

Product 1

HCID 109972345-Amino-2-chlorobenzonitrileYield 91.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
120 °C

Procedure

Conc. HCl (15.6 ml) was added dropwise to 2-chloro-5-nitrobenzonitrile (3.38 g, 18.5 mmol) and SnCl2.2H2O (18.9 g, 83.9 mmol, 4.5 eq.) in isopropanol (35 ml). The mixture was heated at 120° C. for 2 h and then cooled to room temperature and made basic using aq. NaOH. The mixture was extracted with dichloromethane, dried over Na2SO4 and filtered through silica gel. Concentration under reduced pressure gave 5-amino-2-chlorobenzonitrile (2.58 g, 91%).

Workup

  1. temperaturecooled to room temperature
  2. extractionThe mixture was extracted with dichloromethane
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered through silica gel
  5. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-74e288f9470f4450a7813718b17cd8e0
Source dataset
uspto-grants-2015_12
Patent number
US09204645B2

Reaction notes

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