Sulfuric Acid → HCID 54724175, compound

HRID 1831896Notes

Reaction equation

HRID 1831896 reaction equation
C([C:4]1[C:5](=[O:20])[N:6]([C:12]2[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:19])[C:7]([CH3:11])=[CH:8][C:9]=1[OH:10])(=O)C.S(=O)(=O)(O)O>C(O)CCC>[Cl:19][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]([Cl:18])[C:12]=1[N:6]1[C:7]([CH3:11])=[CH:8][C:9]([OH:10])=[CH:4][C:5]1=[O:20]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 54724164HCID 54724164, compound

Product 1

HCID 54724175HCID 54724175, compoundYield 25.9%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 3-acetyl-1-(2,6-dichlorophenyl)-4-hydroxy-6-methylpyridin-2(1H)-one 0.7 g (0.002 mol) in n-butanol (3.0 mL) containing sulfuric acid (1.5 mL) was heated at 120° C. for 4 h. The dark reaction mixture was cooled, added ice/water (25 mL), and extracted with EtOAc (2×25 ml). The combined organic extracts were washed with water, dried (Na2SO4), filtered, concentrated under reduced pressure and the resulting material was purified by silica gel flash chromatography using 25% EtOAc in hexanes as the eluent to afford the title compound (0.14 g) as a pale yellow powder: 1H-NMR (CD3OD) δ: 7.6 (m, 2H), 7.48 (m, 1H), 6.10 (dd, 1H), 5.78 (d, 1H, J=2.4 Hz), 1.91 (s, 3H); ES-MS m/z=270 (MH+); HR-MS, m/z calc C12H10NO2Cl2 270.0083, found 270.0103.

Workup

  1. customThe dark reaction mixture
  2. temperaturewas cooled
  3. extractionextracted with EtOAc (2×25 ml)
  4. washThe combined organic extracts were washed with water
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customthe resulting material was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-806ba4dc824e429093b9f84417ee013b
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

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