9-Nitro-2,3-dihydro-4,1-benzoxazepin-5(1H)-one → 9-Amino-2,3-dihydro-4,1-benzoxazepin-5(1H)-one

HRID 1698539Notes

Reaction equation

HRID 1698539 reaction equation
[N+:1]([C:4]1[C:14]2[NH:13][CH2:12][CH2:11][O:10][C:9](=[O:15])[C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[C:14]2[NH:13][CH2:12][CH2:11][O:10][C:9](=[O:15])[C:8]=2[CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 672730729-Nitro-2,3-dihydro-4,1-benzoxazepin-5(1H)-one

Product 1

HCID 672729029-Amino-2,3-dihydro-4,1-benzoxazepin-5(1H)-oneYield 99.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 500 mg (2.42 mmol) of 9-nitro-2,3-dihydro-4,1-benzoxazepin-5(1H)-one in 500 mL of methanol was inerted with nitrogen. To this solution was added 100 mg of 10% palladium on carbon (50% wet) and the reaction was purged with hydrogen and stirred under balloon pressure hydrogen for 6 h. The catalyst was removed by filtration and the filtrate was concentrated in vacuo to give 430 mg (99%) of the title compound.

Workup

  1. customthe reaction was purged with hydrogen
  2. customThe catalyst was removed by filtration
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-19ace845a53e44c3a014e99d98a360ee
Source dataset
uspto-grants-2012_04
Patent number
US08163935B2

Reaction notes

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