Tetrahydrofuran → 5-(Boc-amino)-2-methylaniline

HRID 1800739Notes

Reaction equation

HRID 1800739 reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([N+:15]([O-])=O)[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].O1CCCC1>C(O)C.[C].[Pd]>[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([NH2:15])[CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 18954623tert-Butyl (4-methyl-3-nitrophenyl)carbamate

Product 1

HCID 246997865-(Boc-amino)-2-methylanilineYield 99.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of tert-butyl(4-methyl-3-nitrophenyl)carbamate (10.1 g, 39.8 mmol) in ethanol (60 mL)/tetrahydrofuran (20 mL) was added 10% palladium-carbon (2.12 g), and the mixture was stirred at room temperature under a hydrogen atmosphere (3 atm) for 22 hr. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure to give the title compound (8.82 g, 99%) as a colorless solid.

Workup

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

Sources & evidence

ORD record
ord-2fdbb0f5f4ce4f92b9af48c8ab3c7227
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

Loading…