2-Tert-butyl-4-(2-ethoxyphenyl)-5-nitrophenol → 2-Tert-butyl-4-(2-ethoxyphenyl)-5-aminophenol

HRID 74004Notes

Reaction equation

HRID 74004 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17][CH2:18][CH3:19])[C:8]([N+:20]([O-])=O)=[CH:7][C:6]=1[OH:23])([CH3:4])([CH3:3])[CH3:2]>CO.[Ni]>[C:1]([C:5]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17][CH2:18][CH3:19])[C:8]([NH2:20])=[CH:7][C:6]=1[OH:23])([CH3:3])([CH3:2])[CH3:4]

Participants

4

Reactant 1

HCID 574702402-Tert-butyl-4-(2-ethoxyphenyl)-5-nitrophenol

Product 1

HCID 574702422-Tert-butyl-4-(2-ethoxyphenyl)-5-aminophenolYield 92%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-tert-butyl-4-(2-ethoxyphenyl)-5-nitrophenol (3.0 g, 9.5 mmol) in methanol (30 ml) was added Raney Ni (300 mg). The mixture was stirred under H2 (1 atm) at room temperature for 2 h. The catalyst was filtered off and the filtrate was concentrated. The residue was purified by column chromatography (petroleum ether-ethyl acetate, 6:1) to afford 2-tert-butyl-4-(2-ethoxyphenyl)-5-aminophenol (C-15) (2.35 g, 92%). 1H NMR (DMSO-d6) δ 8.89 (s, 1H), 7.19 (t, 1H, J=4.2 Hz), 7.10 (d, 1H, J=1.8 Hz), 7.08 (d, 1H, J=1.8 Hz), 6.94 (t, 1H, J=3.6 Hz), 6.67 (s, 1H), 6.16 (s, 1H), 4.25 (s, 1H), 4.00 (q, 2H, J=6.9 Hz), 1.26 (s, 9H), 1.21 (t, 3H, J=6.9 Hz); ESI-MS 286.0 m/z (MH+).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by column chromatography (petroleum ether-ethyl acetate, 6:1)

Sources & evidence

ORD record
ord-0963d1e24a3c4731ad615c1ed2e6ff1f
Source dataset
uspto-grants-2014_09
Patent number
US08829204B2

Reaction notes

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