7-nitro-3,4-dihydro-2H-1,4-benzoxazin-3-one → 7-amino-3,4-dihydro-2H-1,4-benzoxazin-3-one

HRID 641943

Reaction equation

HRID 641943 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[NH:12][C:11](=[O:13])[CH2:10][O:9][C:8]=2[CH:14]=1)([O-])=O.[H][H]>CN(C=O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]2[NH:12][C:11](=[O:13])[CH2:10][O:9][C:8]=2[CH:14]=1

Participants

5

Reactant 2

HCID 27638307-nitro-3,4-dihydro-2H-1,4-benzoxazin-3-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 27641827-amino-3,4-dihydro-2H-1,4-benzoxazin-3-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

Into 500 mL 3-necked round bottom flask was added a solution of 7-nitro-2H-benzo[b][1,4]oxazin-3(4H)-one (12 g, 61.86 mmol) in DMF (150 mL). To the mixture was added Pd/C (5 g) followed by addition of hydrogen gas. The resulting solution was allowed to react, with stirring, overnight while the temperature was maintained at room temperature. The reaction progress was monitored by TLC (ethyl acetate/petroleum ether=1:1). A filtration was performed. The filtrate was concentrated by evaporation under vacuum using a rotary evaporator. The product was precipitated by the addition of H2O. A filtration was performed. The filter cake was washed 3 times with 300 mL of hexane. This resulted in 7.3 g (68%) of 7-amino-2H-benzo[b][1,4]oxazin-3(4H)-one as a yellow solid.

Workup

  1. customto react
  2. filtrationA filtration
  3. concentrationThe filtrate was concentrated by evaporation under vacuum
  4. customa rotary evaporator
  5. customThe product was precipitated by the addition of H2O
  6. filtrationA filtration
  7. washThe filter cake was washed 3 times with 300 mL of hexane
  8. customThis resulted in 7.3 g (68%) of 7-amino-2H-benzo[b][1,4]oxazin-3(4H)-one as a yellow solid

Sources & evidence

ORD record
ord-7a75ea99eb954f7386661d1c4dcd07e8
Source dataset
uspto-grants-2010_04
Patent number
US07696229B2

Linked notes

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