2-Aminobenzonitrile → 16348-49-5

HRID 1418357Notes

Reaction equation

HRID 1418357 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C[O-].[Na+].Cl.[NH2:14][OH:15]>CO>[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4](=[N:14][OH:15])[NH2:5]

Participants

5

Reactant 3

HCID 729132-AminobenzonitrileHCID 443297Hydroxyamine hydrochlorideHCID 10942334Sodium Methoxide

Product 1

HCID 363347816348-49-5

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 2-aminobenzonitrile (10 g, 0.084 mol), sodium methoxide (4.65 g, 0.084 mol) and hydroxylamine hydrochloride (5.88 g, 0.048 mol) in methanol was heated under reflux for 18 hours. The mixture was concentrated to an oil which was partitioned between ethyl acetate and 10% sodium hydroxide solution. The basic phase was separated and extracted three times with ethyl acetate. The combined organic solution was washed three times with saturated brine and dried over magnesium sulphate. Evaporation of the solvent gave the product as an oil which was purified by flash column chromatography on silica gel, eluting with dichloromethane/ethanol as eluant to afford the product as an oil (7.3 g), MS (+FAB) 152 ([M+H]+), 1H NMR (CDCl3) 7.3-6.7 (4H, m), 5.1-4.7 (4H, br, s).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 hours
  3. concentrationThe mixture was concentrated to an oil which
  4. customwas partitioned between ethyl acetate and 10% sodium hydroxide solution
  5. customThe basic phase was separated
  6. extractionextracted three times with ethyl acetate
  7. washThe combined organic solution was washed three times with saturated brine
  8. dry with materialdried over magnesium sulphate
  9. customEvaporation of the solvent

Sources & evidence

ORD record
ord-b8431c2015ae413b93d4c4b5e8722a98
Source dataset
uspto-grants-1999_03
Patent number
US05883102

Reaction notes

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