Sulfuric Acid → HCID 178424504, compound

HRID 2368688

Reaction equation

HRID 2368688 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:17])[CH2:11][C:12](=O)[CH:13]([CH3:15])[CH3:14].OS(O)(=O)=O>>[CH: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:17])[CH:11]=1)([CH3:15])[CH3:14]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 86669288N-(2,5-dimethylphenyl)-4-methyl-3-oxopentanamide

Product 1

HCID 178424504HCID 178424504, compound

Procedure

A sample of N-(2,5-dimethylphenyl)-4-methyl-3-oxopentanamide and 10.0 mL of H2SO4 was reacted at 100° C. for 1 hour. After the reaction was cooled to room temperature it was quenched into ice-H2O. The resulting mixture was extracted with CH2Cl2 (3×20 mL). The combined organic extracts were washed with saturated NaHCO3 (3×15 mL), brine (lx 20 mL), dried over MgSO4 and concentrated. The residue was recrystallized in EtOAc to give 1.30 g of the desired 4-isopropyl-5,8-dimethylquinolin-2-ol. Spectroscopic data: 1H NMR (300 MHz, CDCl3) δ ppm 1.29 (d, J=6.45 Hz, 6 H) 2.41 (s, 3 H) 2.77 (s, 3 H) 3.84 (quin, J=6.59 Hz, 1 H) 6.67 (s, 1 H) 6.93 (d, J=7.62 Hz, 1 H) 7.19 (d, J=7.62 Hz, 1 H) 8.81 (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 saturated NaHCO3 (3×15 mL), brine (lx 20 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was recrystallized in EtOAc

Sources & evidence

ORD record
ord-85e57c4e150a42c790032e490a5b5ba6
Source dataset
uspto-grants-2014_04
Patent number
US08703797B2

Linked notes

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