2,2-difluoro-6-nitro-2H-benzo[b][1,4]oxazin-3(4H)-one → HCID 22061146, compound

HRID 1038813Notes

Reaction equation

HRID 1038813 reaction equation
[F:1][C:2]1([F:16])[O:7][C:6]2[CH:8]=[CH:9][C:10]([N+:12]([O-])=O)=[CH:11][C:5]=2[NH:4][C:3]1=[O:15]>CO.[Pd]>[NH2:12][C:10]1[CH:9]=[CH:8][C:6]2[O:7][C:2]([F:16])([F:1])[C:3](=[O:15])[NH:4][C:5]=2[CH:11]=1

Participants

4

Reactant 1

HCID 594105342,2-difluoro-6-nitro-2H-benzo[b][1,4]oxazin-3(4H)-one2×

Product 1

HCID 22061146HCID 22061146, compoundYield 66.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

In a flask, 10% Pd/C (0.819 g, 0.769 mmol) was added. The flask was placed under vacuum and purged with N2 three times and then MeOH (25 mL) was added. To the flask was added a solution of 2,2-difluoro-6-nitro-2H-benzo[b][1,4]oxazin-3(4H)-one (5.90 g, 25.6 mmol, WO2008024634A1, Page 161, Intermediate C) in MeOH (20 mL). The mixture was then evacuated, purged with N2 and evacuated again. The mixture was placed under an atmosphere of H2 and stirred at rt for about 16 h. The mixture was placed under vacuum and purged with N2 three times. The mixture was filtered over a Celite Pad®, washed with MeOH (300 mL) and concentrated under reduced pressure to give 6-amino-2,2-difluoro-2H-benzo[b][1,4]oxazin-3(4H)-one (3.4 g, 66%); LC/MS (Table 2, Method c) Rt=1.42 min.; MS m/z: 201 (M+H)+.

Workup

  1. custompurged with N2 three times
  2. additionMeOH (25 mL) was added
  3. customThe mixture was then evacuated
  4. custompurged with N2
  5. customevacuated again
  6. custompurged with N2 three times
  7. filtrationThe mixture was filtered over a Celite Pad®
  8. washwashed with MeOH (300 mL)
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4302671c27ad4653b0d83ee9a30cbf28
Source dataset
uspto-grants-2013_10
Patent number
US08551981B2

Reaction notes

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