Water → HCID 66562187, compound

HRID 512097Notes

Reaction equation

HRID 512097 reaction equation
[CH2:1]([C:11]1[C:16](=[O:17])[CH:15]=[C:14]([CH3:18])O[C:12]=1[CH3:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].Cl.[NH2:21][OH:22].C([O-])(=O)C.[Na+].O>C(O)C>[CH2:1]([C:11]1[C:16](=[O:17])[CH:15]=[C:14]([CH3:18])[N:21]([OH:22])[C:12]=1[CH3:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 86710147HCID 86710147, compound

Product 1

HCID 66562187HCID 66562187, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 21 (200 mg, 0.75 mmol), hydroxylamine hydrochloride (1.05 g, 15.2 mmol), sodium acetate (1.24 g, 15.2 mmol), water (1 mL), and ethanol (2 mL) was heated at reflux for 3 days. After the reaction mixture was cooled to room temperature, the crude was concentrated under diminished pressure to afford a yellow oil. The residue was purified by chromatography on a silica gel column. Elution with 5:1 chloroform/methanol gave 3-decyl-1-hydroxy-2,6-dimethylpyridin-4(1H)-one (CPD-7) as a light yellow oil: yield 0.08 g (40%); silica gel TLC Rf 0.4 (3:1 ethyl acetate/methanol); 1H NMR (CDCl3, 400 MHz) δ 0.84-0.88 (m, 3H), 1.24-1.44 (m, 16H), 2.27 (s, 3H), 2.48 (s, 3H), 2.57-2.61 (m, 2H) and 6.65 (s, 1H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 days
  3. concentrationthe crude was concentrated under diminished pressure
  4. customto afford a yellow oil
  5. customThe residue was purified by chromatography on a silica gel column
  6. washElution with 5:1 chloroform/methanol

Sources & evidence

ORD record
ord-6e044ad07d534ac8bad61c7259b0b522
Source dataset
uspto-grants-2015_08
Patent number
US09102626B2

Reaction notes

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