Hydrochloric Acid → 1-Phenyl-2-(pyridin-3-yl)ethanone

HRID 1430601Notes

Reaction equation

[O:1]=[C:2]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH:3]([C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1)C(OCC)=O.Cl>O>[C:15]1([C:2](=[O:1])[CH2:3][C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Ethyl 3-oxo-3-phenyl-2-(pyridin-3-yl)propanoate (1.82 g, 6.76 mmol) was dissolved in hydrogen chloride (8.11 mL, 101.0 mmol) and heated to 100° C. overnight. The reaction was then diluted with H2O (25 mL), extracted with EtOAc (3×50 mL), dried over MgSO4, filtered and concentrated. The residue was purified by silica gel column chromatography to give the title compound as a clear oil (0.894 g). LCMS m/z=198.3 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 4.29 (s, 2H), 7.27 (dd, J=7.07, 5.56 Hz, 1H), 7.49 (t, J=7.58 Hz, 2H), 7.55-7.64 (m, 2H), 7.99-8.05 (m, 2H), 8.49-8.56 (m, 2H).

Workup

extractionextracted with EtOAc (3×50 mL)
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-9f801e22960e449a959b712815a09663
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940891B2

Reaction notes

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