(4-chlorophenyl)hydrazine

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: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: The expected acid is obtained in the form of a white solid with a yield of 11% by following a procedure analogous to Example 1 and starting from 4-chlorophenylhydrazine and ethyl δ-oxobenzenepentanoate.

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

Procedure: This compound was prepared by the same methodology described for EXAMPLE 1 with 4-chlorophenyl hydrazine.HCl substituted for phenyl hydrazine. There was obtained 1-(4′-chlorophenyl)-3-methyl-1H-pyrazole-5-[(2′-aminosulfonyl-[1,1′]-biphen-4-yl)carboxyamide; HRMS (M+H)+: calc. 467.094465; found 467.093532. This compound was prepared by the same methodology

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

Procedure: A mixture of 10.43 g 2-aminoacetophenone and 11.0 g 4-chlorophenylhydrazine in 30 ml EtOH and 10 ml HOAc was refluxed for one hour. The cooled reaction mixture was diluted with water and the precipitate was collected, washed with water, and dried to give 16.83 g solid. Recrystallization from methanol gave 3.48 g solid, m.p. 109°-112° C. was refluxed for one hour The cooled reaction mixture the precipitate was collected washed with water dried

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

Procedure: To a stirred suspension of dimethyl-7-chloro-4-hydroxyquinoline-2,3-dicarboxylate (2.50 g, 8.45 mM) and 4-chlorophenylhydrazine (10.60 g, 59.20 mM) in ethanol (50 mL) was added triethylamine (9.43 mL) to give a brown solution. This solution was refluxed for 24 hours and then cooled to room temperature. Dilution with water (25 mL) gave a brown precipitate. This suspension was stirred for 16 hours and filtered to remove the solids which were discarded. The filtrate formed another precipitate after standing for seven days. This solid was collected and washed with aqueous methanol (50%) and ether to give the 4-chlorophenylhydrazine salt of the title compound as a brown powder (1.20 g). This material was refluxed in glacial acetic acid (25 mL) for 3 hours and cooled to room temperature. The resulting orange suspension was filtered, and the solids were washed with glacial acetic acid and ether to give the title compound (0.810 g, 25%) as a light orange powder, mp 399-401° C.; MS(CI): 374 (M+H). to give a brown solution This solution was refluxed for 24 hours filtered to remove the solids which The filtrate formed another precipitate after standing for seven days This solid was collected washed with aqueous methanol (50%) and ether

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

Procedure: The title compound was prepared following the procedure described for 12a using 11a and 4-chlorophenylhydrazine. 1H-NMR (DMSO-d6) δ (ppm): 7.48 (2H, d, m), 8.20 (2H, m), 8.26 (1H, dd, J=8.61, 2.08 Hz), 8.40 (1H, d, J=8.61 Hz), 8.52 (1H, d, J=2.08 Hz), 8.92 (1H, s). m/z 341.8 (MH+).

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

Procedure: The title compound was prepared following the procedure described for 12a using 11a and 4-chlorophenylhydrazine. 1H-NMR (DMSO-d6) δ (ppm): 7.48 (2H, d, m), 8.20 (2H, m), 8.26 (1H, dd, J=8.61, 2.08 Hz), 8.40 (1H, d, J=8.61 Hz), 8.52 (1H, d, J=2.08 Hz), 8.92 (1H, s). m/z 341.8 (MH+).

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

Procedure: The title compound was prepared following the procedure described for 5a using 4-chlorophenylhydrazine instead of phenylhydrazine. 1H-NMR (DMSO-d6) δ (ppm): 7.50 (2H, d, J=8.91 Hz), 7.90 (1H, d, J=8.91 Hz), 8.29 (2H, d, J=8.91 Hz), 8.48 (1H, dd, J=8.91, 2.38 Hz), 8.88 (1H, s), 8.91 (1H, d, J=2.67 Hz). m/z 341.8 (MH+).