Acetic Acid → 3-(benzyloxy)-1-(4-butylphenyl)pyridin-4(1H)-one

HRID 571046Notes

Reaction equation

HRID 571046 reaction equation
[CH2:1]([C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[CH2:12]([O:19][C:20]1[C:21](=[O:29])[CH:22]=[C:23](C(O)=O)O[CH:25]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CC(O)=O>O>[CH2:12]([O:19][C:20]1[C:21](=[O:29])[CH:22]=[CH:23][N:9]([C:8]2[CH:7]=[CH:6][C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[CH:11][CH:10]=2)[CH:25]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 76944-ButylanilineHCID 64807825-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid

Product 1

HCID 674195993-(benzyloxy)-1-(4-butylphenyl)pyridin-4(1H)-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 4-butylaniline (0.6 g, 4.1 mmol) and 5-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid (1.0 g, 4.1 mmol) in a 1:1 mixture of AcOH:water (4 mL) was heated in a sealed reaction vessel at 120° C. for 72 h. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure, diluted with 10 mL 10% aq. NaOH, and extracted with EtOAc (3×10 mL). The organic fractions were pooled, dried (Na2SO4), and concentrated under reduced pressure to provide 3-(benzyloxy)-1-(4-butylphenyl)pyridin-4(1H)-one, which was used in the subsequent step without further purification. LC/MS (M+H)+ 334.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additiondiluted with 10 mL 10% aq. NaOH
  3. extractionextracted with EtOAc (3×10 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fa4b12df1ed64313b4ac5c9090e3be8c
Source dataset
uspto-grants-2015_05
Patent number
US09024032B2

Reaction notes

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