N-(2,5-dimethylphenyl)-3-oxobutanamide → HCID 178424527, compound

HRID 2368702Notes

Reaction equation

HRID 2368702 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[NH:9][C:10](=[O:15])[CH2:11][C:12](=O)[CH3:13]>OS(O)(=O)=O>[CH3:13][C:12]1[C:4]2[C:3](=[C:2]([CH3:1])[CH:7]=[CH:6][C:5]=2[CH3:8])[N:9]=[C:10]([OH:15])[CH:11]=1

Participants

3

Reactant 1

HCID 284876N-(2,5-dimethylphenyl)-3-oxobutanamide

Product 1

HCID 178424527HCID 178424527, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A 5.50 g (26.8 mmol) sample of N-(2,5-dimethylphenyl)-3-oxobutanamide in 10.0 mL of H2SO4 was microwaved at 140° C. for 5 minutes. After the reaction was cooled to room temperature it was quenched into ice-H2O. The resulting mixture was basified with saturated NaHCO3. The resulting mixture was extracted with CH2Cl2 (3×20 mL) and the combined organic extracts were washed with H2O (1×15 mL), brine (lx 20 mL), dried over MgSO4 and concentrated to give the desired title compound (1.4 g, 28%). Spectroscopic data: 1H NMR (300 MHz, CDCl3) δ ppm 2.41 (s, 3 H) 2.69 (d, J=1.17 Hz, 3 H) 2.73 (s, 3 H) 6.48 (s, 1 H) 6.90 (d, J=7.33 Hz, 1 H) 7.19 (d, J=7.62 Hz, 1 H) 8.87 (br. s., 1 H).

Workup

  1. customwas quenched into ice-H2O
  2. extractionThe resulting mixture was extracted with CH2Cl2 (3×20 mL)
  3. washthe combined organic extracts were washed with H2O (1×15 mL), brine (lx 20 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4c9b4d87a4dc4c0c90b1b4e1c887e47b
Source dataset
uspto-grants-2014_04
Patent number
US08703797B2

Reaction notes

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