O-Methylhydroxylamine → Furo[2,3-b]pyridin-3(2H)-one O-methyloxime

HRID 1508188Notes

Reaction equation

HRID 1508188 reaction equation
[O:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3](=O)[CH2:2]1.[CH3:11][O:12][NH2:13].CC([O-])=O.[Na+]>CCO>[CH3:11][O:12][N:13]=[C:3]1[C:4]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[O:1][CH2:2]1

Participants

5

Reactant 3

HCID 4113O-MethylhydroxylamineHCID 517045Sodium AcetateHCID 125140462H,3H-furo(2,3-b)pyridin-3-one

Product 1

HCID 72248887Furo[2,3-b]pyridin-3(2H)-one O-methyloxime

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of furo[2,3-b]pyridine-3(2H)-one (78.3 mmol) [J. Heterocyclic Chem., 23, 1465 (1986)] in 500 mL EtOH were added O-methyl-hydroxylamine (157 mmol) and NaOAc (157 mmol). After heating to reflux for 2 h the reaction mixture was concentrated in vacuo to half of its volume. Water and DCM were added and the aqueous phase was extracted 3 times with DCM. The combined organic layers were dried over MgSO4 and concentrated in vacuo. Purification by CC using Hept/EtOAc (5/1 to 1/1) gives the desired product as yellow oil;

Workup

  1. temperatureAfter heating
  2. temperatureto reflux for 2 h the reaction mixture
  3. concentrationwas concentrated in vacuo to half of its volume
  4. additionWater and DCM were added
  5. extractionthe aqueous phase was extracted 3 times with DCM
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customPurification by CC

Sources & evidence

ORD record
ord-f87fab5cc5b8415288e9a7983cf33fad
Source dataset
uspto-grants-2015_12
Patent number
US09221832B2

Reaction notes

Loading…