Acetic Acid → 4-{(E)-2-[3-(3-Chlorophenyl)-1H-pyrazol-5-yl]ethenyl}phenol

HRID 2369820Notes

Reaction equation

Cl.Cl.[NH2:3][NH2:4].[Cl:5][C:6]1[CH:7]=[C:8]([C:12](=O)/[CH:13]=[C:14](\O)/[CH:15]=[CH:16]/[C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)[CH:9]=[CH:10][CH:11]=1.C(O)(=O)C>C(O)C>[Cl:5][C:6]1[CH:7]=[C:8]([C:12]2[CH:13]=[C:14](/[CH:15]=[CH:16]/[C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=3)[NH:4][N:3]=2)[CH:9]=[CH:10][CH:11]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Hydrazine dihydro-chloride (0.263 g, 2.50 mmol) was added to a sealed tube charged with (2Z,4E)-1-(3-chlorophenyl)-3-hydroxy-5-(4-hydroxyphenyl)penta-2,4-dien-1-one (0.717 g, 2.39 mmol) in absolute ethanol (8 mL) and a catalytic amount of acetic acid. The reaction tube was sealed and heated to 80° C. After 12 hours the reaction was cooled to room temperature and concentrated in vacuo. The residue was dissolved in a small amount of methanol and precipitated with water, and the solid was collected by vacuum filtration to provide the title compound in (288 mg, 41% yield) as a yellow solid: 1H NMR (400 MHz, CD3OD): δ 7.79 (bs, 1H), 7.68 (bd, J=7.6 Hz, 1H), 7.37 (m, 3H), 7.29 (bd, J=7.6 Hz, 1H), 7.12 (d, J=16.4 Hz, 1H), 6.86 (d, J=16.4 Hz, 1H), 6.81 (bs, 1H), 6.77 (m, 2H); MS (EI) for C17H13 ClN2O: 297.1 (MH+).

Workup

customThe reaction tube was sealed
temperatureAfter 12 hours the reaction was cooled to room temperature
concentrationconcentrated in vacuo
dissolutionThe residue was dissolved in a small amount of methanol
customprecipitated with water
filtrationthe solid was collected by vacuum filtration

Sources & evidence

ORD record: ord-6a667392d3334c38b0164c37a3d28db6
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08710038B2

Reaction notes

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