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

HRID 970649Notes

Reaction equation

HRID 970649 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-fdf69f2b5c9e405e81e7696c299c832e
Source dataset
uspto-grants-2007_12
Patent number
US07312233B2

Reaction notes

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