(3-chloro-4-fluorophenyl)hydrazine;hydrochloride

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

Procedure: 560 mg (2.14 mmol) of the compound of Example 19A is reacted analogously to the synthesis of the compound of Example 20A with 464 mg (2.36 mmol) of 3-chloro-4-fluorophenylhydrazine hydrochloride. After hydrolysis, 488 mg (65% of theory) of the title compound is obtained.

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

Procedure: 1.13 g (3.25 mmol) of the compound of Example 18A is reacted analogously to the synthesis of the compound of Example 20A with 961 mg (4.88 mmol) of 3-chloro-4-fluorophenylhydrazine hydrochloride. After hydrolysis, 576 mg (44% of theory) of the title compound is obtained.

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

Procedure: 1.13 g (3.25 mmol) of the compound of Example 18A is reacted analogously to the synthesis of the compound of Example 20A with 961 mg (4.88 mmol) of 3-chloro-4-fluorophenylhydrazine hydrochloride. After hydrolysis, 576 mg (44% of theory) of the title compound is obtained.

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

Procedure: 220 mg (0.64 mmol) of the compound of Example 17A is reacted analogously to the synthesis of the compound of Example 20A with 188 mg (0.96 mmol) of 3-chloro-4-fluorophenylhydrazine hydrochloride. After hydrolysis, 120 mg (49% of theory) of the title compound is obtained.

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

Procedure: 600 mg (1.33 mmol) of the compound of Example 16A is reacted analogously to the synthesis of the compound of Example 20A with 288 mg (1.46 mmol) of 3-chloro-4-fluorophenylhydrazine hydrochloride. After hydrolysis, the entire reaction mixture is reduced to the dry state i. vac. 712 mg (37% purity, 57% of theory) of the title compound, which is used without further purification, is obtained. After hydrolysis the entire reaction mixture 712 mg (37% purity, 57% of theory) of the title compound, which is used without further purification is obtained

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

Procedure: 600 mg (1.33 mmol) of the compound of Example 16A is reacted analogously to the synthesis of the compound of Example 20A with 288 mg (1.46 mmol) of 3-chloro-4-fluorophenylhydrazine hydrochloride. After hydrolysis, the entire reaction mixture is reduced to the dry state i. vac. 712 mg (37% purity, 57% of theory) of the title compound, which is used without further purification, is obtained. After hydrolysis the entire reaction mixture 712 mg (37% purity, 57% of theory) of the title compound, which is used without further purification is obtained

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

Procedure: 240 mg (0.86 mmol) of the compound of Example 15A is reacted analogously to the synthesis of the compound of Example 20A with 253 mg (1.29 mmol) of 3-chloro-4-fluorophenylhydrazine hydrochloride. After hydrolysis, 16 mg (5% of theory) of the title compound is obtained.

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

Procedure: 240 mg (0.86 mmol) of the compound of Example 15A is reacted analogously to the synthesis of the compound of Example 20A with 253 mg (1.29 mmol) of 3-chloro-4-fluorophenylhydrazine hydrochloride. After hydrolysis, 16 mg (5% of theory) of the title compound is obtained.

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

Procedure: 1.70 g (4.24 mmol) of the compound of Example 14A is reacted analogously to the synthesis of the compound of Example 20A with 1.25 g (6.36 mmol) of 3-chloro-4-fluorophenylhydrazine hydrochloride. After hydrolysis, 896 mg (60% of theory) of the title compound is obtained.

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

Procedure: 1.42 g (4.33 mmol) of the compound of Example 13A is reacted analogously to the synthesis of the compound of Example 20A with 1.28 g (6.50 mmol) of 3-chloro-4-fluorophenylhydrazine hydrochloride. After hydrolysis, 854 mg (59% of theory) of the title compound is obtained.

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

Procedure: 1.42 g (4.33 mmol) of the compound of Example 13A is reacted analogously to the synthesis of the compound of Example 20A with 1.28 g (6.50 mmol) of 3-chloro-4-fluorophenylhydrazine hydrochloride. After hydrolysis, 854 mg (59% of theory) of the title compound is obtained.

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

Procedure: In a 500 ml round bottom flask provided with efficient stirring and external cooling arrangement, 51 ml (, 0.5 mole) of conc. HCl was cooled to below 5 deg C and 25 gms (0.13 mole) 3-chloro-4-fluoroaniline was added. The hydrochloride thus precipitated was then diazotised below 0 deg C with 12 gms (0.17 mole)sodium nitrite and the resulting diazonium salt was decomposed with 100 gms (0.79 mole)sodium sulphite and 12 ml caustic lye. The reaction mixture was filtered to remove impurities.225 ml conc. HCl was added and stirred well and allowed to stand overnight. The 3-chloro-4-fluorophenylhydrazine hydrochloride thus precipitated was filtered and recrystallized from water. The dried product was 18 gms (yield 69%) M.pt: decomposed at 193 deg C. IR (KBr) cm−1 2939 and 2690(NH), 1506 (C═C), 1114 (C—F), 744(C—Cl) In a 500 ml round bottom flask provided The hydrochloride thus precipitated diazotised below 0 deg C The reaction mixture was filtered to remove impurities 225 ml conc. HCl was added stirred well The 3-chloro-4-fluorophenylhydrazine hydrochloride thus precipitated was filtered recrystallized from water decomposed at 193 deg C