Tetrahydrofuran → 2-Oxo-2,3-dihydro-1H-pyrido[3,4-b][1,4]oxazine-7-carbaldehyde

HRID 1437350Notes

Reaction equation

HRID 1437350 reaction equation
[OH:1][CH2:2][C:3]1[N:13]=[CH:12][C:6]2[O:7][CH2:8][C:9](=[O:11])[NH:10][C:5]=2[CH:4]=1.C1COCC1>[O-2].[O-2].[Mn+4].ClCCCl>[O:11]=[C:9]1[CH2:8][O:7][C:6]2[CH:12]=[N:13][C:3]([CH:2]=[O:1])=[CH:4][C:5]=2[NH:10]1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 21873679HCID 21873679, compound

Product 1

HCID 218736022-Oxo-2,3-dihydro-1H-pyrido[3,4-b][1,4]oxazine-7-carbaldehyde

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 111,2-DichloroethaneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of the hydroxymethyloxazinone (h) (584 mg), manganese dioxide (2.3 g), THF (50 ml) and 1,2-dichloroethane (50 ml) was heated at 60° C. under argon for 20 hours. Filtration through kieselguhr and evaporation of solvent gave a solid which was triturated under EtOAc/hexane 1:3, filtered off and dried (383 mg).

Workup

  1. filtrationFiltration
  2. customthrough kieselguhr and evaporation of solvent
  3. customgave a solid which
  4. customwas triturated under EtOAc/hexane 1:3
  5. filtrationfiltered off
  6. customdried (383 mg)

Sources & evidence

ORD record
ord-da07e9a5c0f947f68be1017a0335149a
Source dataset
uspto-grants-2009_11
Patent number
US07622481B2

Reaction notes

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