(4-Tert-butyl-3-nitro-phenyl)-carbamic acid tert-butyl ester → (3-Amino-4-tert-butyl-phenyl)-carbamic acid tert-butyl ester

HRID 2404753Notes

Reaction equation

HRID 2404753 reaction equation
[C:1]([O:5][C:6](=[O:21])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])=[C:10]([N+:18]([O-])=O)[CH:9]=1)([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6](=[O:21])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])=[C:10]([NH2:18])[CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 66675534(4-Tert-butyl-3-nitro-phenyl)-carbamic acid tert-butyl ester

Product 1

HCID 51358180(3-Amino-4-tert-butyl-phenyl)-carbamic acid tert-butyl esterYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of (4-tert-butyl-3-nitro-phenyl)-carbamic acid tert-butyl ester (3.0 g, 10.19 mol) and 10% Pd—C (1 g) in MeOH (40 mL) was stirred under H2 (1 atm) at room temperature overnight. After filtration, the filtrate was concentrated and the residue was purified by column chromatograph (petroleum ether-EtOAc, 5:1) to give (3-amino-4-tert-butyl-phenyl)-carbamic acid tert-butyl ester (D-10) as a brown oil (2.5 g, 93%). 1H NMR (CDCl3) δ 7.10 (d, J=8.4 Hz, 1H), 6.92 (s, 1H), 6.50-6.53 (m, 1H), 6.36 (s, 1H), 3.62 (br s, 2H), 1.50 (s, 9H), 1.38 (s, 9H); ESI-MS 528.9 m/z (2M+H+).

Workup

  1. filtrationAfter filtration
  2. concentrationthe filtrate was concentrated
  3. customthe residue was purified by column chromatograph (petroleum ether-EtOAc, 5:1)

Sources & evidence

ORD record
ord-26db53dc210648e393f47cc3a6065e99
Source dataset
uspto-grants-2014_08
Patent number
US08802700B2

Reaction notes

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