Hydrazine, (2-fluorophenyl)-, hydrochloride (1:1) → HCID 118431879, compound

HRID 2208068Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:23])[C:4](=O)[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:20][CH3:21])[CH:14]=2)=[CH:9][CH:8]=1.Cl.[F:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[NH:32][NH2:33]>C(O)(=O)C>[CH3:1][O:2][C:3]([C:4]1[CH2:5][CH:6]([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:20][CH3:21])[CH:14]=3)=[CH:9][CH:8]=2)[N:32]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[F:25])[N:33]=1)=[O:23]

Participants

Conditions

Temperature: 125 °C

Procedure

4-(3′-Ethoxy-biphenyl-4-yl)-2-oxo-3-butenoic acid methyl ester (190.0 mg, 0.61 mmol) prepared in Step 3 of Preparation 18 and 2-fluorophenylhydrazine hydrochloride (110.0 mg, 0.67 mmol) were added to acetic acid (3.0 mL). The reaction mixture was stirred at 125° C. for 1 hour and then concentrated under reduced pressure. Ethyl acetate was added to the reaction mixture, which was washed with a saturated solution of sodium hydrogen carbonate, dried on anhydrous magnesium sulfate, and then concentrated under reduced pressure to give a yellow liquid residue. The resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/5) to give 250.0 mg of the titled compound as a yellow liquid.

Workup

concentrationconcentrated under reduced pressure
additionEthyl acetate was added to the reaction mixture, which
washwas washed with a saturated solution of sodium hydrogen carbonate
dry with materialdried on anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customto give a yellow liquid residue
customThe resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/5)

Sources & evidence

ORD record: ord-fab91209eba343a1910a668ad65cf44e
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376420B2

Reaction notes

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