TERT-BUTYL METHYL(3-NITROPHENYL)CARBAMATE → tert-butyl N-(3-aminophenyl)-N-methylcarbamate

HRID 1887049Notes

Reaction equation

HRID 1887049 reaction equation
[CH3:1][N:2]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-])=O)[CH:11]=1)[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6]>[Pd].C1COCC1.CO>[NH2:16][C:12]1[CH:11]=[C:10]([N:2]([CH3:1])[C:3](=[O:9])[O:4][C:5]([CH3:6])([CH3:7])[CH3:8])[CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 1

HCID 11528945TERT-BUTYL METHYL(3-NITROPHENYL)CARBAMATE

Product 1

HCID 11492276tert-butyl N-(3-aminophenyl)-N-methylcarbamateYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A round-bottom flask containing tert-butyl methyl(3-nitrophenyl)carbamate (19) (8.8 g, 34.9 mmol), 10% palladium on charcoal (880 mg), and THF-MeOH (80 mL/80 mL) was evacuated and flushed with hydrogen three times. The mixture was stirred vigorously overnight under an atmosphere of hydrogen. The catalyst was removed by filtration through a pad of Celite, and the filtrate evaporated to afford tert-butyl 3-aminophenyl(methyl)carbamate (20) 7 g as yellow solid (yield 91%). LC-MS (ESI): m/z (M+1) 223.

Workup

  1. customwas evacuated
  2. customflushed with hydrogen three times
  3. customThe catalyst was removed by filtration through a pad of Celite
  4. customthe filtrate evaporated

Sources & evidence

ORD record
ord-e4be14dfe3e7477985408fbeef8a0153
Source dataset
uspto-grants-2013_08
Patent number
US08501724B1

Reaction notes

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