Water → HCID 66562188, compound

HRID 1051153Notes

Reaction equation

HRID 1051153 reaction equation
[CH2:1]([C:17]1[C:22](=[O:23])[CH:21]=[C:20]([CH3:24])O[C:18]=1[CH3:25])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].Cl.[NH2:27][OH:28].C([O-])(=O)C.[Na+].O>C(O)C>[CH2:1]([C:17]1[C:22](=[O:23])[CH:21]=[C:20]([CH3:24])[N:27]([OH:28])[C:18]=1[CH3:25])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 86710145HCID 86710145, compound

Product 1

HCID 66562188HCID 66562188, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2 (200 mg, 0.57 mmol), hydroxylamine hydrochloride (399 mg, 5.7 mmol), sodium acetate (471 mg, 5.7 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 product was concentrated under diminished pressure to a yellow oil. The residue was purified by chromatography on a silica gel column. Elution with 5:1 chloroform/methanol gave 3-hexadecyl-1-hydroxy-2,6-dimethylpyridin-4(1H)-one (CPD-8) as a white solid: yield 0.088 g (42%); silica gel TLC Rf 0.5 (3:1 ethyl acetate/methanol); 1H NMR (CDCl3, 400 MHz) δ 0.83-0.85 (m, 3H), 1.22-1.27 (m, 28H), 2.32 (s, 3H), 2.46 (s, 3H), 2.55 (t, 2H, J=8 Hz) and 6.7 (s, 1H).

Workup

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

Sources & evidence

ORD record
ord-a9af16c542f94d06854e42255b5165e2
Source dataset
uspto-grants-2016_07
Patent number
US09388163B2

Reaction notes

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