Water → HCID 66562186, compound

HRID 512096Notes

Reaction equation

HRID 512096 reaction equation
[CH2:1]([C:8]1[C:13](=[O:14])[CH:12]=[C:11]([CH3:15])O[C:9]=1[CH3:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].Cl.[NH2:18][OH:19].C([O-])(=O)C.[Na+].O>C(O)C>[CH2:1]([C:8]1[C:13](=[O:14])[CH:12]=[C:11]([CH3:15])[N:18]([OH:19])[C:9]=1[CH3:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

6

Reactant 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 86710142HCID 86710142, compound

Product 1

HCID 66562186HCID 66562186, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of trimethyl pyrone 1 (113 mg, 0.51 mmol), hydroxylamine hydrochloride (707 mg, 10.2 mmol), sodium acetate (835 mg, 10.2 mmol), water (1 mL), and ethanol (2 mL) was heated to reflux for 8 hr. After the reaction mixture was cooled to room temperature, filtered, and the filtrate was concentrated under diminished pressure. The residue was purified by chromatography on a silica gel column. Elution with 5:1 ethyl acetate/methanol gave 3-heptyl-1-hydroxy-2,6-dimethylpyridin-4(1H)-one (CPD-6): yield 63 mg (51%); silica gel TLC Rf 0.35 (3:1 ethyl acetate/methanol); 1H NMR (400 MHz, CDCl3) δ 0.84-0.88 (m, 3H), 1.24-1.45 (m, 10H), 2.36 (s, 3H), 2.47 (s, 3H), 2.60 (t, 2H, J=7.6 Hz) and 6.73 (s, 1H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 8 hr
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under diminished pressure
  5. customThe residue was purified by chromatography on a silica gel column
  6. washElution with 5:1 ethyl acetate/methanol

Sources & evidence

ORD record
ord-39fd39097fac4053b5135001a43902d6
Source dataset
uspto-grants-2015_08
Patent number
US09102626B2

Reaction notes

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