Ammonia → 3,4-Dihydro-2H-1,4-benzoxazine

HRID 901937Notes

Reaction equation

HRID 901937 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH3:7].O.[CH2:9]1[CH2:13][O:12][CH2:11][CH2:10]1>>[O:12]1[C:11]2[CH:10]=[CH:13][CH:9]=[CH:10][C:11]=2[NH:7][CH2:9][CH2:13]1

Participants

5

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 8028TetrahydrofuranHCID 21226445Aluminium lithium hydride

Product 1

HCID 5850963,4-Dihydro-2H-1,4-benzoxazineYield 91%

Procedure

2H-1,4-benzoxazin-3-(4M-one (4.5 g, 30 mmol) was added portionwise to a stirred suspension of lithium aluminium hydride (4.7 g, 120 mmol) in THF (100 ml) and heated at reflux for 3 h. The mixture was cooled in an ice/water bath and ammonia solution (8 ml) and water (40 ml) were added while stirring. The mixture was filtered through Celite and reduced. Chromatography (50% EtOAc/50% 60-80 petroleum ether) afforded benzomorpholine (3.7 g, 91%) as a pale brown oil.

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 h
  3. temperatureThe mixture was cooled in an ice/water bath
  4. filtrationThe mixture was filtered through Celite

Sources & evidence

ORD record
ord-b11fc8902946489388c102ca58f8fa8c
Source dataset
uspto-grants-2008_04
Patent number
US07365065B2

Reaction notes

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