tert-Butyl [2-(4-nitrophenoxy)ethyl]carbamate → tert-Butyl [2-(4-aminophenoxy)ethyl]carbamate

HRID 2399882Notes

Reaction equation

HRID 2399882 reaction equation
[CH3:1][C:2]([O:5][C:6](=[O:20])[NH:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=1)([CH3:4])[CH3:3].[H][H]>CO.[Pd]>[CH3:4][C:2]([O:5][C:6](=[O:20])[NH:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[CH:13][C:14]([NH2:17])=[CH:15][CH:16]=1)([CH3:1])[CH3:3]

Participants

5

Reactant 2

HCID 18173671tert-Butyl [2-(4-nitrophenoxy)ethyl]carbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 18173954tert-Butyl [2-(4-aminophenoxy)ethyl]carbamateYield 99.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 775 mg (2.75 mmol) of nitro compound from Example 215 in 20 mL of methanol with 10% palladium on carbon (150 mg) was introduced hydrogen via balloon at room temperature for 4 h. The catalyst was filtered off through Celite, and the filterate was concentrated under vacuum to give 690 mg of the title compound: 1H NMR (200 MHz, CDCl3) 8 6.69 (d, 2H, J=8Hz), 6.58 (d, 2H, J=8Hz), 4.94 (bs, 1H, N-H), 3.89 (bt, 2H, J=5.0Hz), 3.40 (q, 2H, J=5.0Hz), 1.40 (s, 9H).

Workup

  1. filtrationThe catalyst was filtered off through Celite
  2. concentrationthe filterate was concentrated under vacuum

Sources & evidence

ORD record
ord-5dd56f1efd214f57b83f8a9cedba556c
Source dataset
uspto-grants-1995_09
Patent number
US05451677

Reaction notes

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