4-Tert-butyl-2-chloro-5-nitro-phenol → 4-Tert-butyl-2-chloro-5-amino-phenol

HRID 1915319Notes

Reaction equation

HRID 1915319 reaction equation
[C:1]([C:5]1[C:10]([N+:11]([O-])=O)=[CH:9][C:8]([OH:14])=[C:7]([Cl:15])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]>CO.[Ni]>[C:1]([C:5]1[C:10]([NH2:11])=[CH:9][C:8]([OH:14])=[C:7]([Cl:15])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 574702324-Tert-butyl-2-chloro-5-nitro-phenol

Product 1

HCID 574702334-Tert-butyl-2-chloro-5-amino-phenolYield 78%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-tert-butyl-2-chloro-5-nitro-phenol (12.6 g, 54.9 mmol) in MeOH (50 mL) was added Ni (1.2 g). The reaction was shaken under H2 (1 atm) for 4 h. The reaction mixture was filtered and the filtrate was concentrated. The residue was purified by column chromatography (P.E./EtOAc, 20:1) to give 4-tert-butyl-2-chloro-5-amino-phenol (C-11) (8.5 g, 78%). 1H NMR (DMSO-d6) δ 9.33 (s, 1H), 6.80 (s, 1H), 6.22 (s, 1H), 4.76 (s, 1H), 1.23 (s, 9H); ESI-MS 200.1 m/z (MH+).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by column chromatography (P.E./EtOAc, 20:1)

Sources & evidence

ORD record
ord-980adcf37f6d42988c076b240f70ad3d
Source dataset
uspto-grants-2013_12
Patent number
US08614327B2

Reaction notes

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