Toluene → 4-(2-Aminophenyl)butyronitrile

HRID 49658Notes

Reaction equation

HRID 49658 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH2:11][CH2:12][C:13]#[N:14])([O-])=O.[Cl-].[NH4+].C1(C)C=CC=CC=1>CO.O.[Fe]>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH2:11][CH2:12][C:13]#[N:14]

Participants

7

Reactant 3

HCID 1140TolueneHCID 25517Ammonium ChlorideHCID 112177214-(2-Nitrophenyl)butyronitrile

Product 1

HCID 184058244-(2-Aminophenyl)butyronitrile

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

450 mg of 4-(2-nitrophenyl)butyronitrile, dissolved in 12.5 ml of methanol, are added dropwise to a mixture of 412 mg of iron powder (7.5 mmol) and 663 mg of ammonium chloride (12.5 mmol) in 12.5 ml of water at room temperature and under protective gas in a 100 ml glass round-bottomed flask. The mixture is heated for 5 hours with reflux. 25 ml of water are added to the cooled mixture and extraction is performed with toluene. The combined toluene phases are dried and the solvent distilled off under reduced pressure. The residue is purified by column chromatography on silica gel (eluent toluene/ethyl acetate 10:1 v/v). Yield: 276 mg (1.73 mmol, 72%).

Workup

  1. temperatureThe mixture is heated for 5 hours
  2. temperaturewith reflux
  3. dry with materialThe combined toluene phases are dried
  4. distillationthe solvent distilled off under reduced pressure
  5. customThe residue is purified by column chromatography on silica gel (eluent toluene/ethyl acetate 10:1 v/v)

Sources & evidence

ORD record
ord-51255e6d37eb4cd3b6e15cac3ad72da9
Source dataset
uspto-grants-2004_03
Patent number
US06706924B2

Reaction notes

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