p-Toluenesulfonic acid → 2-[3,4-dihydro-2H-pyrido[3,2-b]-1,4-oxazin-4-yl]acetaldehyde

HRID 1375031Notes

Reaction equation

HRID 1375031 reaction equation
[O:1]1CCO[CH:2]1[CH2:6][N:7]1[CH2:12][CH2:11][O:10][C:9]2[CH:13]=[CH:14][CH:15]=[N:16][C:8]1=2.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O.O>[O:10]1[CH2:11][CH2:12][N:7]([CH2:6][CH:2]=[O:1])[C:8]2[N:16]=[CH:15][CH:14]=[CH:13][C:9]1=2

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 179639403,4-dihydro-4-[(1,3-dioxolan-2-yl)methyl]-2H-pyrido[3,2-b]-1,4-oxazine

Product 1

HCID 179639722-[3,4-dihydro-2H-pyrido[3,2-b]-1,4-oxazin-4-yl]acetaldehydeYield 86.3%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of 3,4-dihydro-4-[(1,3-dioxolan-2-yl)methyl]-2H-pyrido[3,2-b]-1,4-oxazine (0.13 g) in acetone (10 ml) and water (1 ml) was heated under reflux in the presence of p-toluenesulfonic acid (2.24 g) for 3 days. The mixture was concentrated in vacuo and the residue was poured into aqueous saturated sodium hydrogen carbonate solution. The water layer was extracted with ethyl acetate three times and the combined organic layers were dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel using a mixed solvent of methanol and dichloromethane (1:10) as an eluent. The fractions containing the objective compound were collected and evaporated under reduced pressure to give 2-[3,4-dihydro-2H-pyrido[3,2-b]-1,4-oxazin-4-yl]acetaldehyde (0.09 g) as an oil.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additionthe residue was poured into aqueous saturated sodium hydrogen carbonate solution
  3. extractionThe water layer was extracted with ethyl acetate three times
  4. dry with materialthe combined organic layers were dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel using a mixed solvent of methanol and dichloromethane (1:10) as an eluent
  7. additionThe fractions containing the objective compound
  8. customwere collected
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-c8c5958e1c38402fb281b123c9096c6c
Source dataset
uspto-grants-2007_01
Patent number
US07166598B2

Reaction notes

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