2-Chloroaniline → HCID 22148450, compound

HRID 1823953Notes

Reaction equation

HRID 1823953 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[Cl:10][C:11]1[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=1[NH2:13].C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.C(OCC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:10][C:11]1[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=1[NH:13][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 72402-ChloroanilineHCID 10796Cesium carbonateHCID 12162Benzonitrile, 4-bromo-

Product 1

HCID 22148450HCID 22148450, compoundYield 36%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-bromobenzonitrile (3.0 g, 16.4 mmol) in toluene (40 mL) is added 2-chloroaniline (2.09 mL, 19.7 mmol), cesium carbonate (7.5 g, 23.0 mmol), palladium (II) acetate (110 mg, 0.50 mmol) and S-BINAP (460 mg, 0.74 mmol). The reaction mixture is then heated to 100° C. for 12 hours under an argon atmosphere. Once complete, the reaction is cooled to room temperature, diluted with diethyl ether and filtered. The filtrate is then concentrated and purified by column chromatography (6% ethyl acetate in hexanes) to afford 1.35 g of 4-[(2-chlorophenyl)amino]benzonitrile.

Workup

  1. temperatureOnce complete, the reaction is cooled to room temperature
  2. filtrationfiltered
  3. concentrationThe filtrate is then concentrated
  4. custompurified by column chromatography (6% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-c70604d006154db1824af78ac3545270
Source dataset
uspto-grants-2006_05
Patent number
US07041690B2

Reaction notes

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