Nitric Acid → 6-Nitro-2H-pyrido[3,2-B][1,4]oxazin-3(4H)-one

HRID 1718223Notes

Reaction equation

HRID 1718223 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.[N+:12]([O-])([OH:14])=[O:13]>C(O)(=O)C.C(OC(=O)C)(=O)C>[N+:12]([C:9]1[CH:10]=[CH:11][C:2]2[O:1][CH2:6][C:5](=[O:7])[NH:4][C:3]=2[N:8]=1)([O-:14])=[O:13]

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 884992H-pyrido(3,2-b)-1,4-oxazin-3(4H)-one

Product 1

HCID 220607326-Nitro-2H-pyrido[3,2-B][1,4]oxazin-3(4H)-one

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 7918Acetic AnhydrideSolvent

Procedure

2H-Pyrido[3,2-b]-1,4-oxazin-3(4H)-one (2.5 g) was dissolved in acetic acid (6 mL) and acetic anhydride (30 mL). Fuming nitric acid (3 mL) was added dropwise to the reaction solution in ice-bath. The reaction solution was stirred in ice-bath overnight. Solution was poured into crashed ice. The light yellow precipitation was collected by filtration, washed with water and dried to give a mixture of nitrated products (regio-isomers). The mixture was crystallized from dichloromethane to give 6-nitro-2H-pyrido[3,2-b]-1,4-oxazin-3(4H)-one (1 g) as a light yellow solid.

Workup

  1. additionSolution was poured
  2. customThe light yellow precipitation
  3. filtrationwas collected by filtration
  4. washwashed with water
  5. customdried
  6. customto give
  7. additiona mixture of nitrated products (regio-isomers)
  8. customThe mixture was crystallized from dichloromethane

Sources & evidence

ORD record
ord-3c4be9d4b08d4045a4f1999697d98e56
Source dataset
uspto-grants-2010_09
Patent number
US07803939B2

Reaction notes

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