[2-(6-Methyl-5-nitro-pyridin-2-yloxy)-ethyl]-propyl-carbamic Acid Tert-Butyl Ester → [2-(5-Amino-6-methyl-pyridin-2-yloxy)-ethyl]-propyl-carbamic Acid Tert-Butyl Ester

HRID 390308Notes

Reaction equation

HRID 390308 reaction equation
[C:1]([O:5][C:6](=[O:24])[N:7]([CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[C:16]([CH3:23])[N:15]=1)[CH2:8][CH2:9][CH3:10])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6](=[O:24])[N:7]([CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[C:16]([CH3:23])[N:15]=1)[CH2:8][CH2:9][CH3:10])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 66883393[2-(6-Methyl-5-nitro-pyridin-2-yloxy)-ethyl]-propyl-carbamic Acid Tert-Butyl Ester

Product 1

HCID 66881282[2-(5-Amino-6-methyl-pyridin-2-yloxy)-ethyl]-propyl-carbamic Acid Tert-Butyl EsterYield 84.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of [2-(6-methyl-5-nitro-pyridin-2-yloxy)-ethyl]-propyl-carbamic acid tert-butyl ester (300 mg, 0.88 mmol) in methanol (10 ml) was hydrogenated using the ThalesNano H-Cube® hydrogenation reactor employing a 10% palladium on charcoal catalyst cartridge. After concentration of the solution under reduced pressure, 230 mg (84.2%) of the title compound were obtained.

Sources & evidence

ORD record
ord-8b43234660954cb0884c5e7e2b3db1a1
Source dataset
uspto-grants-2013_02
Patent number
US08383641B2

Reaction notes

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