Tetrahydrofuran → tert-butyl N-(3-aminophenyl)carbamate

HRID 1800713Notes

Reaction equation

HRID 1800713 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-])=O)[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].O1CCCC1>C(O)C.[C].[Pd]>[C:1]([O:5][C:6](=[O:17])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([NH2:14])[CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 10514065Tert-butyl 3-nitrophenylcarbamate

Product 1

HCID 12877220tert-butyl N-(3-aminophenyl)carbamateYield 98.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of tert-butyl(3-nitrophenyl)carbamate (17.1 g, 71.7 mmol) in ethanol (90 mL)/tetrahydrofuran (30 mL) was added 10% palladium-carbon (1.53 g), and the mixture was stirred at room temperature under a hydrogen atmosphere (3 atm) for 9 hr. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was washed with diethyl ether/hexane mixture to give the title compound (14.7 g, 98%) as a colorless solid.

Workup

  1. filtrationThe insoluble material was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. washThe obtained residue was washed with diethyl ether/hexane mixture

Sources & evidence

ORD record
ord-7af70f8f5eae4a5591208561e4bbfe8b
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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