6-Nitro-2H-1,4-benzoxazin-3(4H)-one → 6-amino-3,4-dihydro-2H-1,4-benzoxazin-3-one

HRID 2102947Notes

Reaction equation

HRID 2102947 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]2[O:8][CH2:9][C:10](=[O:12])[NH:11][C:6]=2[CH:5]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:14]=[CH:13][C:7]2[O:8][CH2:9][C:10](=[O:12])[NH:11][C:6]=2[CH:5]=1

Participants

4

Reactant 1

HCID 27636836-Nitro-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 27636816-amino-3,4-dihydro-2H-1,4-benzoxazin-3-oneYield 56%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Pd/C (10%) was added to a suspension of 6-nitro-2H-benzo[b][1,4]oxazin-3(4H)-one (1.5 g) in MeOH (20 mL) and the reaction mixture was stirred under an atmosphere of hydrogen overnight. The mixture was filtered through Celite® and the filtrate was concentrated under vacuum to give the product (0.705 g, 56%) as a beige solid.

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-20a8c65adf864b3bac8b0c5efc8f905d
Source dataset
uspto-grants-2009_08
Patent number
US07576099B2

Reaction notes

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