Acetic Acid → 3-Amino-2-bromobenzonitrile

HRID 61847Notes

Reaction equation

HRID 61847 reaction equation
[Br:1][C:2]1[C:9]([N+:10]([O-])=O)=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C(O)(=O)C.[OH-].[Na+]>C(O)C.O.[Fe]>[NH2:10][C:9]1[C:2]([Br:1])=[C:3]([CH:6]=[CH:7][CH:8]=1)[C:4]#[N:5]

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 131624152-Bromo-3-nitrobenzonitrile

Product 1

HCID 601554243-Amino-2-bromobenzonitrile

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

2-Bromo-3-nitro-benzonitrile (Compound U1, 678 mg, 2.987 mmol) was dissolved in ethanol (20.9 mL) and water (8.96 mL), added with acetic acid (2.39 mL, 41.81 mmol) and iron (1.17 g, 20.91 mmol), and stirred at 60° C. for 18 hr. The reaction solution was poured into aqueous solution of sodium hydroxide (1 M), extracted with ethyl acetate, washed with water and saturated brine, dried over sodium sulfate, and then filtered. After concentration under reduced pressure, 3-amino-2-bromo-benzonitrile (Compound U2) was obtained as a crude product.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water and saturated brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationAfter concentration under reduced pressure

Sources & evidence

ORD record
ord-b06b7329751e4c5aa846618c97bb8cb7
Source dataset
uspto-grants-2016_09
Patent number
US09440922B2

Reaction notes

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