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

HRID 2278138Notes

Reaction equation

HRID 2278138 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-649fc1ec98d44501ad0dff6c8375c74c
Source dataset
uspto-grants-2015_09
Patent number
US09133133B2

Reaction notes

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