Methyl iodide → 4-methyl-2,3-dihydro-4H-pyrido[3,2-b][1,4]oxazin-3-one

HRID 1109468Notes

Reaction equation

HRID 1109468 reaction equation
[O:1]1[CH2:6][C:5](=[O:7])[NH:4][C:3]2[N:8]=[CH:9][CH:10]=[CH:11][C:2]1=2.[H-].[Na+].[CH3:14]I.[Cl-].[NH4+]>CN(C=O)C>[CH3:14][N:4]1[C:5](=[O:7])[CH2:6][O:1][C:2]2[CH:11]=[CH:10][CH:9]=[N:8][C:3]1=2

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 884992H-pyrido(3,2-b)-1,4-oxazin-3(4H)-one

Product 1

HCID 155374514-methyl-2,3-dihydro-4H-pyrido[3,2-b][1,4]oxazin-3-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,3-Dihydro-4H-pyrido[3,2-b][1,4]oxazin-3-one (U.S. Pat. No. 3,854,926; 1.5 g) was added portionwise to a stirred suspension of sodium hydride (60% w/w dispersion in mineral oil; 0.4 g) in DMF (30 ml) which had been cooled in an ice-bath. The mixture was allowed to warm to ambient temperature and was stirred for 30 minutes. Methyl iodide (0.65 ml) was added and the mixture was stirred at ambient temperature for 16 hours. The mixture was poured into a saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic phase was washed with water and with brine, dried (MgSO4) and evaporated to give 4-methyl-2,3-dihydro-4H-pyrido[3,2-b][1,4]-oxazin-3-one (1.58 g) which was used without further purification.

Workup

  1. temperaturehad been cooled in an ice-bath
  2. stirringthe mixture was stirred at ambient temperature for 16 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with water and with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-0a1c1ac5680a45838ab787575645ba72
Source dataset
uspto-grants-1994_06
Patent number
US05321025

Reaction notes

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