Pyridine → HCID 86589855, compound

HRID 1826085Notes

Reaction equation

HRID 1826085 reaction equation
[CH2:1]([CH:3]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12](C=O)[CH:11]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].Cl.[NH2:21][OH:22].N1C=CC=CC=1>C(O)C>[CH2:1]([CH:3]([CH2:9][C:10]1[CH2:11][C:12](=[N:21][OH:22])[C:13]([O:16][CH3:17])=[CH:14][CH:15]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 11010838HCID 11010838, compound

Product 1

HCID 86589855HCID 86589855, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 2-ethyl-3-(3-formyl-4-methoxyphenyl)propanoate (1.06 g, 4.01 mmol), hydroxylamine hydrochloride (293 mg, 4.22 mmol), pyridine (1 mL) and ethanol (20 mL) was refluxed for 6 hours. After cooling, the mixture was concentrated and the residue was dissolved in ethyl acetate, which was washed with 1 mol/L hydrochloric acid, saturated aqueous solution of sodium hydrogencarbonate and brine, dried over anhydrous sodium sulfate, and then concentrated. The residue was purified by silica gel column chromatography (eluent: n-hexane:ethyl acetate=6:1 v/v) to afford 1.00 g (89%) of the title compound as a pale yellow oil.

Workup

  1. temperaturewas refluxed for 6 hours
  2. temperatureAfter cooling
  3. concentrationthe mixture was concentrated
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washwhich was washed with 1 mol/L hydrochloric acid, saturated aqueous solution of sodium hydrogencarbonate and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography (eluent: n-hexane:ethyl acetate=6:1 v/v)

Sources & evidence

ORD record
ord-410f5fec491348f195ecf20c9dae3058
Source dataset
uspto-grants-2006_05
Patent number
US07049342B2

Reaction notes

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