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

HRID 528417Notes

Reaction equation

HRID 528417 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:8][CH2:9][C:10](=[O:14])[NH:11][C:12]=2[N:13]=1)([O-])=O>CO.Cl.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]2[O:8][CH2:9][C:10](=[O:14])[NH:11][C:12]=2[N:13]=1

Participants

5

Reactant 1

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

Product 1

HCID 220605636-amino-2H,3H,4H-pyrido[3,2-b][1,4]oxazin-3-one

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

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. 6-Nitro-2H-pyrido[3,2-b]-1,4-oxazin-3(4H)-one (1 g) was reduced under hydrogenolysis conditions using 10% Pd—C in methanol (50 mL) and 1N HCl solution (10 mL) at 50 psi for 2 h. The catalyst was filtered off and washed with methanol and 1N HCl solution. The filtrate was evaporated to give 6-amino-2H-pyrido[3,2-b]-1,4-oxazin-3(4H)-one.

Workup

  1. customfor 2 h
  2. filtrationThe catalyst was filtered off
  3. washwashed with methanol and 1N HCl solution
  4. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-b1bc70f503db4ec0b8ee0ad7bd8befa3
Source dataset
uspto-grants-2016_05
Patent number
US09346765B2

Reaction notes

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