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

HRID 1617634
Notes
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Reaction equation

HRID 1617634 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 670155693-(4-Bromo-phenyl)-1-(6-methoxy-pyridin-3-yl)-3-o-tolyl-propan-1-one

Product 1

HCID 666688905-[3-(4-Bromo-phenyl)-3-o-tolyl-propionyl]-1H-pyridin-2-oneYield 91.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

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

  1. temperatureAfter cooling to room temperature
  2. additionthe mixture was poured into ice
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes