2-chloro-1-(1H-indol-3-yl)ethanone

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

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

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

Conditions: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: According to the method of J. Bergman et al. Tet. 29, 971-976 (1973), combine indole (11.7 g, 100 mmol), pyridine (8.1 mL, 100 mmol), and toluene (250 mL). Heat to 55° C. Add dropwise a solution of chloroacetyl chloride (8 mL, 100 mmol) in toluene (10 mL). After 2 hours, cool to ambient temperature. Dilute the reaction mixture with ethyl acetate and extract with water. Dry the organic layer over MgSO4, filter and evaporate in vacuo to give a residue. Recrystallize the residue from ethanol to give the title compound. cool to ambient temperature extract with water Dry the organic layer over MgSO4 filter evaporate in vacuo to give a residue Recrystallize the residue from ethanol

Conditions: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: According to the method of J. Bergman et al. Tet. 29, 971-976 (1973), combine indole (11.7 g, 100 mmol), pyridine (8.1 mL, 100 mmol), and toluene (250 mL). Heat to 55° C. Add dropwise a solution of chloroacetyl chloride (8 mL, 100 mmol) in toluene (10 mL). After 2 hours, cool to ambient temperature. Dilute the reaction mixture with ethyl acetate and extract with water. Dry the organic layer over MgSO4, filter and evaporate in vacuo to give a residue. Recrystallize the residue from ethanol to give the title compound. cool to ambient temperature extract with water Dry the organic layer over MgSO4 filter evaporate in vacuo to give a residue Recrystallize the residue from ethanol

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

Conditions: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: According to the method of J. Bergman et al. Tet. 29, 971-976 (1973), combine indole (11.7 g, 100 mmol), pyridine (8.1 mL, 100 mmol), and toluene (250 mL). Heat to 55° C. Add dropwise a solution of chloroacetyl chloride (8 mL, 100 mmol) in toluene (10 mL). After 2 hours, cool to ambient temperature. Dilute the reaction mixture with ethyl acetate and extract with water. Dry the organic layer over MgSO4, filter and evaporate in vacuo to give a residue. Recrystallize the residue from ethanol to give the title compound. cool to ambient temperature extract with water Dry the organic layer over MgSO4 filter evaporate in vacuo to give a residue Recrystallize the residue from ethanol

Conditions: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: According to the method of J. Bergman et al. Tet. 29, 971-976 (1973), combine indole (11.7 g, 100 mmol), pyridine (8.1 mL, 100 mmol), and toluene (250 mL). Heat to 55° C. Add dropwise a solution of chloroacetyl chloride (8 mL, 100 mmol) in toluene (10 mL). After 2 hours, cool to ambient temperature. Dilute the reaction mixture with ethyl acetate and extract with water. Dry the organic layer over MgSO4, filter and evaporate in vacuo to give a residue. Recrystallize the residue from ethanol to give the title compound. cool to ambient temperature extract with water Dry the organic layer over MgSO4 filter evaporate in vacuo to give a residue Recrystallize the residue from ethanol

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

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

Conditions: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of 6.00 g (51.2 mmole) indole and 4.2 ml (47.5 mmole) pyridine in 50 ml toluene at 55° C. was added dropwise 5.85 g (51.8 mmole) chloroacetyl chloride. The resulting orange-colored mixture was stirred at 55° C. for 90 minutes and cooled to room temperature. Water (150 ml) and methanol (25 ml) were added and the mixture stirred for another hour. The precipitate was collected, washed with water (50 ml) and dried to give 10.18 g of crude product. This was triturated with chloroform, filtered, the solid washed with chloroform and crystallized from methanol to afford 2.35 g (23%) of product; m.p. 236°-237° C. Reworking the mother liquors gave a second crop which was purified by flash chromatography on silica gel. Two recrystallizations of this product gave an analytically pure product; m.p. 236°-237° C. cooled to room temperature the mixture stirred for another hour The precipitate was collected washed with water (50 ml) dried to give 10.18 g of crude product This was triturated with chloroform filtered the solid washed with chloroform crystallized from methanol

Conditions: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: According to the method of J. Bergman et al. Tet. 29, 971-976 (1973), combine indole (11.7 g, 100 mmol), pyridine (8.1 mL, 100 mmol), and toluene (250 mL). Heat to 55° C. Add dropwise a solution of chloroacetyl chloride (8 mL, 100 mmol) in toluene (10 mL). After 2 hours, cool to ambient temperature. Dilute the reaction mixture with ethyl acetate and extract with water. Dry the organic layer over MgSO4, filter and evaporate in vacuo to give a residue. Recrystallize the residue from ethanol to give the title compound. cool to ambient temperature extract with water Dry the organic layer over MgSO4 filter evaporate in vacuo to give a residue Recrystallize the residue from ethanol