cycloheptane-1,2-dione

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Cycloheptane-1,2-dione (1 g, 7.9 mmol) was dissolved in MeOH (25 mL) and (2,4-dichlorophenyl)hydrazine hydrochloride (1.86 g, 8.7 mmol) in AcOH—HCl (3.5:1, 45 mL) was added and heated to 60° C. for 18 h. MeOH was removed in vacuo, the reaction mixture was basified with aqueous NaHCO3 (pH-8) and then extracted with EtOAc (3×25 mL), The combined organic extracts were dried over Na2SO4 and concentrated under reduced pressure to give the crude product which was purified by silica gel chromatograph [EtOAc-hexane (9:1) as eluant] to give the title compound (0.2 g, 9.4%). 1H NMR (200 MHz, CDCl3, δ in ppm) 9.0 (br s, 1H), 7.54 (d, J=1.6 Hz, 1H), 7.33 (d, J=1.8 Hz, 1H), 3.11 (t, J=12.0 Hz, 2H), 2.90 (t, J=11.8 Hz, 2H), 2.13-2.20 (m, 4H). MeOH was removed in vacuo extracted with EtOAc (3×25 mL) The combined organic extracts were dried over Na2SO4 concentrated under reduced pressure to give the crude product which was purified by silica gel chromatograph [EtOAc-hexane (9:1) as eluant]

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Cycloheptane-1,2-dione (1 g, 7.9 mmol) was dissolved in MeOH (25 mL) and (2,4-dichlorophenyl)hydrazine hydrochloride (1.86 g, 8.7 mmol) in AcOH—HCl (3.5:1, 45 mL) was added and heated to 60° C. for 18 h. MeOH was removed in vacuo, the reaction mixture was basified with aqueous NaHCO3 (pH-8) and then extracted with EtOAc (3×25 mL), The combined organic extracts were dried over Na2SO4 and concentrated under reduced pressure to give the crude product which was purified by silica gel chromatograph [EtOAc-hexane (9:1) as eluant] to give the title compound (0.2 g, 9.4%). 1H NMR (200 MHz, CDCl3, δ in ppm) 9.0 (br s, 1H), 7.54 (d, J=1.6 Hz, 1H), 7.33 (d, J=1.8 Hz, 1H), 3.11 (t, J=12.0 Hz, 2H), 2.90 (t, J=11.8 Hz, 2H), 2.13-2.20 (m, 4H). MeOH was removed in vacuo extracted with EtOAc (3×25 mL) The combined organic extracts were dried over Na2SO4 concentrated under reduced pressure to give the crude product which was purified by silica gel chromatograph [EtOAc-hexane (9:1) as eluant]

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

Procedure: light brown solid. MS (EI): 227.2 (M+). Prepared from cycloheptane-1,2-dione, [2-(1-Methyl-1H-pyrrol-2-yl)-2-oxo-ethyl]-phosphonic acid dimethyl ester, hydrazine monohydrate.

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

Procedure: light brown solid. MS (EI): 272.2 (M+). Prepared from cycloheptane-1,2-dione, [2-(4-Chloro-2-methyl-phenyl)-2-oxo-ethyl]-phosphonic acid dimethyl ester, hydrazine monohydrate.

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

Procedure: light brown solid. MS (EI): 272.2 (M+). Prepared from cycloheptane-1,2-dione, [2-(4-Chloro-2-methyl-phenyl)-2-oxo-ethyl]-phosphonic acid dimethyl ester, hydrazine monohydrate.

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

Procedure: light yellow solid. MS (EI): 238.2 (M+). Prepared from cycloheptane-1,2-dione, (2-Oxo-2-o-tolyl-ethyl)-phosphonic acid dimethyl ester, hydrazine monohydrate.

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

Procedure: light yellow gum. MS (ESI): 255.2 (MH+). Prepared from cycloheptane-1,2-dione, [2-(2-Methoxy-phenyl)-2-oxo-ethyl]-phosphonic acid dimethyl ester, hydrazine monohydrate.

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

Procedure: light yellow gum. MS (ESI): 255.2 (MH+). Prepared from cycloheptane-1,2-dione, [2-(2-Methoxy-phenyl)-2-oxo-ethyl]-phosphonic acid dimethyl ester, hydrazine monohydrate.

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Cycloheptane-1,2-dione (1 g, 7.9 mmol) was dissolved in MeOH (25 mL) and (2,4-dichlorophenyl)hydrazine hydrochloride (1.86 g, 8.7 mmol) in AcOH—HCl (3.5:1, 45 mL) was added and heated to 60° C. for 18 h. MeOH was removed in vacuo, the reaction mixture was basified with aqueous NaHCO3 (pH-8) and then extracted with EtOAc (3×25 mL), The combined organic extracts were dried over Na2SO4 and concentrated under reduced pressure to give the crude product which was purified by silica gel chromatograph [EtOAc-hexane (9:1) as eluant] to give the title compound (0.2 g, 9.4%). 1H NMR (200 MHz, CDCl3, δ in ppm) 9.0 (br s, 1H), 7.54 (d, J=1.6 Hz, 1H), 7.33 (d, J=1.8 Hz, 1H), 3.11 (t, J=12.0 Hz, 2H), 2.90 (t, J=11.8 Hz, 2H), 2.13-2.20 (m, 4H). MeOH was removed in vacuo extracted with EtOAc (3×25 mL) The combined organic extracts were dried over Na2SO4 concentrated under reduced pressure to give the crude product which was purified by silica gel chromatograph [EtOAc-hexane (9:1) as eluant]