Hydrochloric Acid → 5-[3-(4-Bromo-phenyl)-3-o-tolyl-propionyl]-1H-pyridin-2-one

HRID 1617634Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH3:26])[CH2:9][C:10]([C:12]2[CH:13]=[N:14][C:15]([O:18]C)=[CH:16][CH:17]=2)=[O:11])=[CH:4][CH:3]=1.Cl>O1CCOCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH3:26])[CH2:9][C:10]([C:12]2[CH:17]=[CH:16][C:15](=[O:18])[NH:14][CH:13]=2)=[O:11])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 3-(4-bromo-phenyl)-1-(6-methoxy-pyridin-3-yl)-3-o-tolyl-propan-1-one (384 mg) in 1,4-dioxane (16 ml) was added concentrated aqueous HCl (17 ml). The mixture was stirred for 1.5 h at 100° C. After cooling to room temperature, the mixture was poured into ice and extracted with ethyl acetate. The organic phase was dried (MgSO4), filtered and concentrated to dryness. The product was purified by chromatography (SiO2, dichloromethane/methanol 1:0 to 9:1) to give the title compound (338 mg) as a colorless foam, MS (ESI−): m/z=393.8 [M−H]−.

Workup

temperatureAfter cooling to room temperature
additionthe mixture was poured into ice
extractionextracted with ethyl acetate
dry with materialThe organic phase was dried (MgSO4)
filtrationfiltered
concentrationconcentrated to dryness
customThe product was purified by chromatography (SiO2, dichloromethane/methanol 1:0 to 9:1)

Sources & evidence

ORD record: ord-85d3e4debee84a1ea4a16442e0278677
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765730B2

Reaction notes

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