Tetrahydrofuran → HCID 57387079, compound

HRID 1800619Notes

Reaction equation

HRID 1800619 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:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][N:16]=2)[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].O1CCCC1>C(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:20]=[CH:19][C:18]([NH2:21])=[CH:17][N:16]=2)[CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 91373956HCID 91373956, compound

Product 1

HCID 57387079HCID 57387079, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of the above-mentioned crude product tert-butyl{3-[(5-nitropyridin-2-yl)oxy]phenyl}carbamate in ethanol (80 mL)/tetrahydrofuran (20 mL) was added 10% palladium-carbon (1.54 g), and the mixture was stirred at room temperature for 7 hr under a hydrogen atmosphere (1.0 pressure). The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was recrystallized from methanol to give the title compound (3.35 g, 77%) as brown crystals.

Workup

  1. filtrationThe insoluble material was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe obtained residue was recrystallized from methanol

Sources & evidence

ORD record
ord-e05e11a34c8047389822b94b081b3320
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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