Sodium Hydroxide → 2-Amino-4-bromobenzonitrile

HRID 968571

Reaction equation

HRID 968571 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([N+:10]([O-])=O)[CH:3]=1.[OH-].[Na+]>Cl>[NH2:10][C:4]1[CH:3]=[C:2]([Br:1])[CH:9]=[CH:8][C:5]=1[C:6]#[N:7]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 2925354-Bromo-2-nitrobenzonitrile

Product 1

HCID 99206362-Amino-4-bromobenzonitrile

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a suspension of 4-bromo-2-nitro-benzonitrile (2.60 g, 0.0115 mol) in 12N HCl at 0° C., add SnCl2-2H2O portionwise. As the reaction is stirred vigorously, a white precipitate will form. After 1 h add ice to the reaction vessel followed by 10N NaOH until the solution is basic. Extract the aqueous mixture with ether (2×) and EtOAc (1×) and wash the combined organic layers with brine. Dry the solution (Na2SO4) and remove the solvents under reduced pressure to give 2-amino-4-bromo-benzonitrile as a beige solid.

Workup

  1. customa white precipitate will form
  2. additionAfter 1 h add ice to the reaction vessel
  3. extractionExtract the aqueous mixture with ether (2×) and EtOAc (1×)
  4. washwash the combined organic layers with brine
  5. dry with materialDry the solution (Na2SO4)
  6. customremove the solvents under reduced pressure

Sources & evidence

ORD record
ord-7dda7b7f49c8475baa86c98a934738a0
Source dataset
uspto-grants-2007_12
Patent number
US07304059B2

Linked notes

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