4-Chloroaniline → HCID 178449876, compound

HRID 75484Notes

Reaction equation

HRID 75484 reaction equation
[C:1](#[N:5])[CH2:2][CH2:3][CH3:4].[Al+3].[Cl-].[Cl-].[Cl-].[Cl:10][C:11]1[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=1>C1(C)C=CC=CC=1.O>[Cl:10][C:11]1[CH:17]=[CH:16][C:14]([NH:15][C:1](=[NH:5])[CH2:2][CH2:3][CH3:4])=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 78124-Chloroaniline2×HCID 8008Butyronitrile2×HCID 6451240Aluminum(III) Chloride

Product 1

HCID 178449876HCID 178449876, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
115 °C

Procedure

To a solution of butyronitrile (compound 2, 7.5 mL, 86.2 mmol), AlCl3 in toluene was added 4-chloroaniline (compound 1, 10.0 g, 78.4 mmol). The reaction mixture was stirred at 115° C. for 5 hrs. The mixture was diluted with water (200 mL) and extracted with EtOAc (200 mL) The aqueous layer was neutralized with saturated NaHCO3 (500 mL) and extracted with EtOAc (300 mL×2). The organic layer was dried over anhydrous MgSO4, filtered and concentrated in vacuo. The obtained product (9.2 g, pale brown solid) was used for the next step without purification.

Workup

  1. extractionextracted with EtOAc (200 mL) The aqueous layer
  2. extractionextracted with EtOAc (300 mL×2)
  3. dry with materialThe organic layer was dried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe obtained product (9.2 g, pale brown solid) was used for the next step without purification

Sources & evidence

ORD record
ord-5d9fdc9310e449abab4ec5622bb74e20
Source dataset
uspto-grants-2014_09
Patent number
US08835436B2

Reaction notes

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