2-Chlorophenylhydrazine hydrochloride → HCID 118431700, compound

HRID 2207938Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:16])[C:4](=O)[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[C:9]([F:14])[CH:8]=1.Cl.[Cl:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[NH:25][NH2:26]>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]([Br:13])=[C:9]([F:14])[CH:8]=2)[N:25]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[Cl:18])[N:26]=1)=[O:16]

Participants

Conditions

Temperature: 125 °C

Procedure

4-(4-bromo-3-fluoro-phenyl)-2-oxo-3-butenoic acid methyl ester (665.0 mg, 2.3 mmol) prepared in Step 2 and 2-chlorophenylhydrazine hydrochloride (455.0 mg, 2.6 mmol) were added to acetic acid (10.0 mL). The reaction mixture was stirred at 125° C. for 3 hours, concentrated under reduced pressure, and then ethyl acetate was added thereto. The reaction mixture 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=1/2) to give 835.0 mg of the titled compound as a pale yellow liquid.

Workup

concentrationconcentrated under reduced pressure
additionethyl acetate was added
washThe reaction mixture was 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=1/2)

Sources & evidence

ORD record: ord-e080d7ffa07c4ccfa6f8196e197df20c
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376420B2

Reaction notes

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