2-CHLORO-6-FLUOROPHENYLHYDRAZINE HYDROCHLORIDE

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (2-Chloro-6-fluorophenyl)hydrazine hydrochloride (CAS no. 529512-79-6) (5 g, 25.38 mmol) was partitioned between EtOAc (100 mL) and NaOH (2M, aq) (40 mL). The organic layer separated and washed with water (50 mL), brine (50 mL), dried (MgSO4), filtered and concentrated. The resultant oil was suspended in MeOH (50 mL) under nitrogen at -5° C. 2-(Ethoxymethylene)malononitrile (3.10 g, 25.38 mmol) added portionwise over 5 mins and the mixture stirred at ˜0° C. for 30 mins. The reaction mixture was allowed to warm to room temperature and then heated at reflux under nitrogen for 2 hours. The reaction mixture was allowed to cool and evaporated to dryness to afford the product (3.52 g) which was used without further purification. 529512-79-6) (5 g, 25.38 mmol) was partitioned between EtOAc (100 mL) and NaOH (2M, aq) (40 mL) The organic layer separated washed with water (50 mL), brine (50 mL) dried (MgSO4) filtered concentrated was suspended in MeOH (50 mL) under nitrogen at -5° C to warm to room temperature heated at reflux under nitrogen for 2 hours to cool evaporated to dryness

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (2-Chloro-6-fluorophenyl)hydrazine hydrochloride (CAS no. 529512-79-6) (5 g, 25.38 mmol) was partitioned between EtOAc (100 mL) and NaOH (2M, aq) (40 mL). The organic layer separated and washed with water (50 mL), brine (50 mL), dried (MgSO4), filtered and concentrated. The resultant oil was suspended in MeOH (50 mL) under nitrogen at -5° C. 2-(Ethoxymethylene)malononitrile (3.10 g, 25.38 mmol) added portionwise over 5 mins and the mixture stirred at ˜0° C. for 30 mins. The reaction mixture was allowed to warm to room temperature and then heated at reflux under nitrogen for 2 hours. The reaction mixture was allowed to cool and evaporated to dryness to afford the product (3.52 g) which was used without further purification. 529512-79-6) (5 g, 25.38 mmol) was partitioned between EtOAc (100 mL) and NaOH (2M, aq) (40 mL) The organic layer separated washed with water (50 mL), brine (50 mL) dried (MgSO4) filtered concentrated was suspended in MeOH (50 mL) under nitrogen at -5° C to warm to room temperature heated at reflux under nitrogen for 2 hours to cool evaporated to dryness