Tert-butyl[2-[3-(3-nitro-2-pyridyloxy)phenyl]ethyl]carbamate → Tert-butyl[2-[3-(3-amino-2-pyridyloxy)phenyl]ethyl]carbamate

HRID 1373229Notes

Reaction equation

HRID 1373229 reaction equation
[C:1]([O:5][C:6](=[O:26])[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][C:17]2[C:22]([N+:23]([O-])=O)=[CH:21][CH:20]=[CH:19][N:18]=2)[CH:11]=1)([CH3:4])([CH3:3])[CH3:2]>[C].[Pd].C(O)C>[C:1]([O:5][C:6](=[O:26])[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][C:17]2[C:22]([NH2:23])=[CH:21][CH:20]=[CH:19][N:18]=2)[CH:11]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 21073098Tert-butyl[2-[3-(3-nitro-2-pyridyloxy)phenyl]ethyl]carbamate

Product 1

HCID 21073097Tert-butyl[2-[3-(3-amino-2-pyridyloxy)phenyl]ethyl]carbamateYield 76.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

5% carbon-palladium (3.0 g) was added to an ethanol (100 ml) solution of tert-butyl[2-[3-(3-nitro-2-pyridyloxy)phenyl]ethyl]carbamate (10.1 g, 28 mmols). The resulting mixture was hydrogenated at room temperature under atmospheric pressure. The catalyst was removed through filtration, and the filtrate was concentrated under reduced pressure. Thus was obtained an oil of tert-butyl[2-[3-(3-amino-2-pyridyloxy)phenyl]ethyl]carbamate (7.09 g, 76.9%).

Workup

  1. customwas hydrogenated at room temperature under atmospheric pressure
  2. customThe catalyst was removed through filtration
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1b1400b5c5674108b16ae194c3d6d959
Source dataset
uspto-grants-2007_01
Patent number
US07160887B1

Reaction notes

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