2H-pyrido(3,2-b)-1,4-oxazin-3(4H)-one → 3,4-Dihydro-2H-pyrido(3,2-b)(1,4)oxazine

HRID 225843Notes

Reaction equation

HRID 225843 reaction equation
[O:1]1[CH2:6][C:5](=O)[NH:4][C:3]2[N:8]=[CH:9][CH:10]=[CH:11][C:2]1=2.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[O:1]1[CH2:6][CH2:5][NH:4][C:3]2[N:8]=[CH:9][CH:10]=[CH:11][C:2]1=2

Participants

4

Reactant 2

HCID 884992H-pyrido(3,2-b)-1,4-oxazin-3(4H)-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 131965383,4-Dihydro-2H-pyrido(3,2-b)(1,4)oxazineYield 79.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 2H-pyrido[3,2-b]-1,4-oxazin-3(4H)one (2.0 g, 13.3 mmole) in dry THF (40 mL) was added a solution of LiAlH4 in THF (1.0 M, 26.6 mL, 26.6 mmole) slowly at 0° C. After 1 hr the mixture was quenched with 2.0 M NaOH until a solid formed. The mixture was dried (MgSO4), filtered, and concentrated under reduced pressure to give the title compound (1.44 g, 79%) as a white solid which was sufficiently pure for use in the next step: MS (ES) m/e 137 (M+H)+.

Workup

  1. customAfter 1 hr the mixture was quenched with 2.0 M NaOH until a solid
  2. customformed
  3. dry with materialThe mixture was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-80fba402d64645de879626caec569488
Source dataset
uspto-grants-2009_07
Patent number
US07557125B2

Reaction notes

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