4-chloro-N-propan-2-ylaniline

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 500 ml reaction flask fitted with a condenser, drying tube, magnetic stirrer and therometer was charged with 89.5 g (0.528 mole) of 4-chloro-N-isopropylaniline, 200 ml of glacial acetic acid and 18.5 g (0.58 mole) of mercuric acetate. To the stirred solution there was added dropwise 48.8 g (0.58 mole) of diketene while the reaction temperature was maintained at 30°-5°. The reaction solution was allowed to stir overnight at ambient temperature. The solution was mixed with two liters of water and twice extracted with ether. The organic phase was washed with water and dried over sodium sulfate. After removing the solvent, the liquid residue weighed 134 g (100%). N.M.R. (CDCl3) ∂1.0 and 1.2 (isopropyl, doublet), 1.8 (CH3, enol), 2.1 (CH3, keto), 3.2 (CH2), 4.7-5.2 (CH, isopropyl), 7.1-7.5 (aromatic). A 500 ml reaction flask fitted with a condenser drying tube, magnetic stirrer was maintained at 30°-5° twice extracted with ether The organic phase was washed with water dried over sodium sulfate After removing the solvent

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 500 ml reaction flask fitted with a condenser, drying tube, magnetic stirrer and therometer was charged with 89.5 g (0.528 mole) of 4-chloro-N-isopropylaniline, 200 ml of glacial acetic acid and 18.5 g (0.58 mole) of mercuric acetate. To the stirred solution there was added dropwise 48.8 g (0.58 mole) of diketene while the reaction temperature was maintained at 30°-5°. The reaction solution was allowed to stir overnight at ambient temperature. The solution was mixed with two liters of water and twice extracted with ether. The organic phase was washed with water and dried over sodium sulfate. After removing the solvent, the liquid residue weighed 134 g (100%). N.M.R. (CDCl3) ∂1.0 and 1.2 (isopropyl, doublet), 1.8 (CH3, enol), 2.1 (CH3, keto), 3.2 (CH2), 4.7-5.2 (CH, isopropyl), 7.1-7.5 (aromatic). A 500 ml reaction flask fitted with a condenser drying tube, magnetic stirrer was maintained at 30°-5° twice extracted with ether The organic phase was washed with water dried over sodium sulfate After removing the solvent

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared as described for Compound 546c using Compound 546a in place of 4-chloro-N-methylaniline. MS: 595.27 (M+H+).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1 g (7.84 mmol) of 4-chloroaniline, 0.91 g (15.68 mmol) of acetone, 0.99 g (15.68 mmol) of NaCNBH3, 4 g of MgSO4 in 99 mL anhydrous EtOH and 1 mL AcOH was stirred at room temperature overnight, filtered and the solvent was removed. The residue was dissolved in 50 mL EtOAc, washed with 50 mL H2O, dried (Na2SO4) and evaporated. The residue was purified on silica gel using hexane/EtOAc as eluent to yield 0.86 g colorless oil. MS: 170.08 (M+H+). filtered the solvent was removed The residue was dissolved in 50 mL EtOAc washed with 50 mL H2O dried (Na2SO4) evaporated The residue was purified on silica gel

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 500 ml reaction flask fitted with a condenser, drying tube, magnetic stirrer and therometer was charged with 89.5 g (0.528 mole) of 4-chloro-N-isopropylaniline, 200 ml of glacial acetic acid and 18.5 g (0.58 mole) of mercuric acetate. To the stirred solution there was added dropwise 48.8 g (0.58 mole) of diketene while the reaction temperature was maintained at 30°-5°. The reaction solution was allowed to stir overnight at ambient temperature. The solution was mixed with two liters of water and twice extracted with ether. The organic phase was washed with water and dried over sodium sulfate. After removing the solvent, the liquid residue weighed 134 g (100%). N.M.R. (CDCl3) ∂1.0 and 1.2 (isopropyl, doublet), 1.8 (CH3, enol), 2.1 (CH3, keto), 3.2 (CH2), 4.7-5.2 (CH, isopropyl), 7.1-7.5 (aromatic). A 500 ml reaction flask fitted with a condenser drying tube, magnetic stirrer was maintained at 30°-5° twice extracted with ether The organic phase was washed with water dried over sodium sulfate After removing the solvent

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 500 ml reaction flask fitted with a condenser, drying tube, magnetic stirrer and therometer was charged with 89.5 g (0.528 mole) of 4-chloro-N-isopropylaniline, 200 ml of glacial acetic acid and 18.5 g (0.58 mole) of mercuric acetate. To the stirred solution there was added dropwise 48.8 g (0.58 mole) of diketene while the reaction temperature was maintained at 30°-5°. The reaction solution was allowed to stir overnight at ambient temperature. The solution was mixed with two liters of water and twice extracted with ether. The organic phase was washed with water and dried over sodium sulfate. After removing the solvent, the liquid residue weighed 134 g (100%). N.M.R. (CDCl3) ∂1.0 and 1.2 (isopropyl, doublet), 1.8 (CH3, enol), 2.1 (CH3, keto), 3.2 (CH2), 4.7-5.2 (CH, isopropyl), 7.1-7.5 (aromatic). A 500 ml reaction flask fitted with a condenser drying tube, magnetic stirrer was maintained at 30°-5° twice extracted with ether The organic phase was washed with water dried over sodium sulfate After removing the solvent