4-Chloroaniline → HCID 178446836, compound

HRID 1062420Notes

Reaction equation

HRID 1062420 reaction equation
[CH3:1][CH:2]([CH3:6])[CH2:3][C:4]#[N:5].[Al+3].[Cl-].[Cl-].[Cl-].[Cl:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=1>C1(C)C=CC=CC=1.O>[Cl:11][C:12]1[CH:18]=[CH:17][C:15]([NH:16][C:4](=[NH:5])[CH2:3][CH:2]([CH3:6])[CH3:1])=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 78124-ChloroanilineHCID 12244IsovaleronitrileHCID 6451240Aluminum(III) Chloride

Product 1

HCID 178446836HCID 178446836, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a solution of 3-methylbutanenitrile (250 mg, 3.0 mmol) and AlCl3 (400 mg, 3.0 mmol) in toluene (6 mL) was added 4-chloroaniline (383 mg, 3.0 mmol). The resulting solution was stirred at reflux for 2 h, diluted with water, and extracted with EtOAc. The aqueous layer was neutralized with saturated NaHCO3 solution and extracted with EtOAc. The combined extracts were dried over MgSO4, filtered, and concentrated. The crude product (364 mg, 58% yield) was used for the next step without purification.

Workup

  1. temperatureat reflux for 2 h
  2. extractionextracted with EtOAc
  3. extractionextracted with EtOAc
  4. dry with materialThe combined extracts were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e8724d6cb4a9438c9c3eeb94a9b9a95c
Source dataset
uspto-grants-2005_11
Patent number
US06960601B2

Reaction notes

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