Tetrahydrofuran → Tert-butyl 3-(6-aminopyridin-3-yloxy)phenylcarbamate

HRID 1800397Notes

Reaction equation

HRID 1800397 reaction equation
[C:1]([O:5][C:6](=[O:24])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]2[CH:16]=[N:17][C:18]([N+:21]([O-])=O)=[CH:19][CH:20]=2)[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].O1CCCC1>C(OCC)(=O)C.[C].[Pd]>[C:1]([O:5][C:6](=[O:24])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]2[CH:16]=[N:17][C:18]([NH2:21])=[CH:19][CH:20]=2)[CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 57749209Tert-butyl 3-(6-nitropyridin-3-yloxy)phenylcarbamate

Product 1

HCID 57749334Tert-butyl 3-(6-aminopyridin-3-yloxy)phenylcarbamateYield 108.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl{3-[(6-nitropyridin-3-yl)oxy]phenyl}carbamate (6.00 g, 18.1 mmol) in ethyl acetate (500 mL)/tetrahydrofuran (150 mL) was added 10% palladium-carbon (600 mg), and the mixture was stirred at room temperature for 16 hr under a hydrogen atmosphere (1.0 atm). The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure to give the title compound (5.9 g, quantitative) as a brown oil. The obtained compound was used for the next reaction without further purification.

Workup

  1. filtrationThe insoluble material was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-da3b8d855b8244b68a2a309d96bc16fc
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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