Hydrazine → 5-(2-Chlorophenyl)-4-(4-chlorophenyl)-2-hydrazinylpyridine

HRID 2101395Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[CH:10][C:11](F)=[N:12][CH:13]=1.[NH2:22][NH2:23]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[CH:10][C:11]([NH:22][NH2:23])=[N:12][CH:13]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a suspension of 5-(2-chlorophenyl)-4-(4-chlorophenyl)-2-fluoropyridine (0.32 g, 1 mmol) in pyridine (4 mL) at room temperature was added anhydrous hydrazine (1 mL). The resulting mixture was stirred at 90° C. for 1 hour. Analysis by HPLC/MS indicated the reaction was complete. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. To the residue was added water, and the resulting suspension was extracted with EtOAc (50 mL×3). The combined EtOAc extracts were washed with saturated aqueous NaCl, dried over Na2SO4, filtered and concentrated under reduced pressure to yield 0.28 g of the title compound (85%) as a white foam. HPLC/MS: retention time=3.03 min, [M+H]+=330.1.

Workup

temperatureAfter cooling to room temperature
concentrationthe reaction mixture was concentrated under reduced pressure
additionTo the residue was added water
extractionthe resulting suspension was extracted with EtOAc (50 mL×3)
washThe combined EtOAc extracts were washed with saturated aqueous NaCl
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-6a63ea9a6f2a4b398186386accc2370a
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07572808B2

Reaction notes

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