2-Chlorophenylhydrazine hydrochloride → HCID 118431723, compound

HRID 2207933Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:15])[C:4](=O)[CH:5]=[CH:6][C:7]1[CH:8]=[N:9][C:10]([Br:13])=[CH:11][CH:12]=1.Cl.[Cl:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[NH:24][NH2:25]>C(O)(=O)C>[CH3:1][O:2][C:3]([C:4]1[CH2:5][CH:6]([C:7]2[CH:8]=[N:9][C:10]([Br:13])=[CH:11][CH:12]=2)[N:24]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[Cl:17])[N:25]=1)=[O:15]

Participants

Conditions

Temperature: 125 °C

Procedure

4-(6-bromo-pyridin-3-yl)-2-oxo-3-butenoic acid methyl ester (615.0 mg, 2.3 mmol) prepared in Step 1 and 2-chlorophenylhydrazine hydrochloride (450.0 mg, 2.5 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 650.0 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-c8e6dc22ef4f4716b2694cc3f9787a28
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376420B2

Reaction notes

Loading…