6-Chloro-8-nitro-2H-benzo[b][1,4]oxazin-3(4H)-one → 8-Amino-2H-1,4-benzoxazin-3(4H)-one

HRID 1750144Notes

Reaction equation

HRID 1750144 reaction equation
Cl[C:2]1[CH:12]=[C:11]([N+:13]([O-])=O)[C:5]2[O:6][CH2:7][C:8](=[O:10])[NH:9][C:4]=2[CH:3]=1>CCO.[Pd]>[NH2:13][C:11]1[C:5]2[O:6][CH2:7][C:8](=[O:10])[NH:9][C:4]=2[CH:3]=[CH:2][CH:12]=1

Participants

4

Reactant 1

HCID 116515356-Chloro-8-nitro-2H-benzo[b][1,4]oxazin-3(4H)-one

Product 1

HCID 115934888-Amino-2H-1,4-benzoxazin-3(4H)-oneYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Intermediate 57 (326 mg, 1.4 mmol) was dissolved in EtOH, then Pd/C (0.03 g) was added. The mixture was hydrogenated under H2 for 4 h at 50° C. The reaction mixture was filtered over Hyflo and the filtrate was concentrated in vacuo to give 8-amino-2H-benzo[b][1,4]oxazin-3(4H)-one (intermediate 58) (83%) as a brown solid, which was used in the next step without any further purification.

Workup

  1. filtrationThe reaction mixture was filtered over Hyflo
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-56779accfbdc4bde94a89e23249d27ca
Source dataset
uspto-grants-2015_10
Patent number
US09156822B2

Reaction notes

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