4-(1,3-dioxoisoindol-2-yl)butanoyl chloride

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: 2,7-Bis(4-phthalimidobutyryl)xanthene, prepared from 4-phthalimidobutyryl chloride and xanthene by the method of S. S. Cheng et al., J. Med. Chem. 9, 945 (1966), is treated with 700 ml. of hot glacial acetic acid after which 200 ml. of concentrated hydrochloric acid is added gradually with stirring. The mixture is heated to reflux for 24 hours with a constant stream of HCl gas passing through the mixture The reaction mixture is stirred and refluxed for an additional 24 hours, cooled, and the product worked up in the usual manner. 9, 945 (1966), is treated with 700 ml The mixture is heated is stirred refluxed for an additional 24 hours cooled

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

Procedure: 2,7-Bis(4-phthalimidobutyryl)thioxanthene, prepared from 4-phthalimidobutyryl chloride and thioxanthene by the method of S.S. Cheng et al., J. Med. Chem. 9, 945 (1966), is treated with hot glacial acetic acid after which concentrated HCl is added gradually with stirring. The mixture is heated to reflux for 24 hours with a constant stream of HCl gas passing through the mixture. The reaction mixture is stirred and refluxed for an additional 24 hours, cooled, and the product worked up in the usual manner. is added gradually The mixture is heated The reaction mixture is stirred refluxed for an additional 24 hours cooled

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

Procedure: Aluminum chloride (43 g) is added to a stirred solution of 4-phthalimidobutyryl chloride (36.2 g) in 1,1,2,2-tetrachloroethane (400 ml), previously saturated with acetylene. Acetylene is bubbled through the solution overnight, with stirring, and the reaction mixture is then decomposed by the addition of crushed ice (300 g). The organic layer is separated and the aqueous layer extracted with 1,1,2,2-tetrachloroethane (3 × 100 ml). The combined organic solution is dried over sodium sulphate and concentrated. The residual solid is recrystallized from hexane affording 1-chloro-6-phthalimidohex-1-en-3-one, m.p. 92°C. Acetylene is bubbled through the solution overnight the reaction mixture is then decomposed by the addition of crushed ice (300 g) The organic layer is separated the aqueous layer extracted with 1,1,2,2-tetrachloroethane (3 × 100 ml) The combined organic solution is dried over sodium sulphate concentrated The residual solid is recrystallized from hexane

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

Procedure: Aluminum chloride (43 g) is added to a stirred solution of 4-phthalimidobutyryl chloride (36.2 g) in 1,1,2,2-tetrachloroethane (400 ml), previously saturated with acetylene. Acetylene is bubbled through the solution overnight, with stirring, and the reaction mixture is then decomposed by the addition of crushed ice (300 g). The organic layer is separated and the aqueous layer extracted with 1,1,2,2-tetrachloroethane (3 × 100 ml). The combined organic solution is dried over sodium sulphate and concentrated. The residual solid is recrystallized from hexane affording 1-chloro-6-phthalimidohex-1-en-3-one, m.p. 92°C. Acetylene is bubbled through the solution overnight the reaction mixture is then decomposed by the addition of crushed ice (300 g) The organic layer is separated the aqueous layer extracted with 1,1,2,2-tetrachloroethane (3 × 100 ml) The combined organic solution is dried over sodium sulphate concentrated The residual solid is recrystallized from hexane

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: 31.4 g (0.143 mol) of 8-chloro-1,2,3,4,5,6-hexahydrobenzo[f]quinoline dissolved in 300 ml of methylene chloride are added at 0° to a solution of 36.0 g (0.143 mol) of 4-phthalimidobutyryl chloride in 360 ml of methylene chloride and the mixture is stirred at room temperature for 1 hour. The solution is concentrated, extracted with methylene chloride and aqueous sodium hydrogen carbonate solution dried with magnesium sulfate and the solvent is distilled in a vacuum. Extractive crystallization with acetone gives 8-chloro-1,2,3,4,5,6-hexahydro-4-(4-phthalimidobutyryl)benzo[f]quinoline as white crystals with melting point 182-183°. The solution is concentrated extracted with methylene chloride and aqueous sodium hydrogen carbonate solution dried with magnesium sulfate the solvent is distilled in a vacuum Extractive crystallization with acetone

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

Procedure: 31.4 g (0.143 mol) of 8-chloro-1,2,3,4,5,6-hexahydrobenzo[f]quinoline dissolved in 300 ml of methylene chloride are added at 0° to a solution of 36.0 g (0.143 mol) of 4-phthalimidobutyryl chloride in 360 ml of methylene chloride and the mixture is stirred at room temperature for 1 hour. The solution is concentrated, extracted with methylene chloride and aqueous sodium hydrogen carbonate solution, dried with magnesium sulfate and the solvent is distilled in a vacuum. Extractive crystallization with acetone gives 8-chloro-1,2,3,4,5,6-hexahydro-4-(4-phthalimidobutyryl)benzo[f]quinoline as white crystals with melting point 182°-183°. The solution is concentrated extracted with methylene chloride and aqueous sodium hydrogen carbonate solution dried with magnesium sulfate the solvent is distilled in a vacuum Extractive crystallization with acetone

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

Procedure: 2,7-Bis(4-phthalimidobutyryl)xanthene, prepared from 4-phthalimidobutyryl chloride and xanthene by the method of S. S. Cheng et al., J. Med. Chem. 9, 945 (1966), is treated with 700 ml. of hot glacial acetic acid after which 200 ml. of concentrated hydrochloric acid is added gradually with stirring. The mixture is heated to reflux for 24 hours with a constant stream of HCl gas passing through the mixture The reaction mixture is stirred and refluxed for an additional 24 hours, cooled, and the product worked up in the usual manner. 9, 945 (1966), is treated with 700 ml The mixture is heated is stirred refluxed for an additional 24 hours cooled

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

Procedure: 2,7-Bis(4-phthalimidobutyryl)thioxanthene, prepared from 4-phthalimidobutyryl chloride and thioxanthene by the method of S.S. Cheng et al., J. Med. Chem. 9, 945 (1966), is treated with hot glacial acetic acid after which concentrated HCl is added gradually with stirring. The mixture is heated to reflux for 24 hours with a constant stream of HCl gas passing through the mixture. The reaction mixture is stirred and refluxed for an additional 24 hours, cooled, and the product worked up in the usual manner. is added gradually The mixture is heated The reaction mixture is stirred refluxed for an additional 24 hours cooled