4,6-Di-tert-butyl-3-nitrobenzene-1,2-diol → 3-Amino-4,6-di-tert-butyl-benzene-1,2-diol

HRID 401353Notes

Reaction equation

HRID 401353 reaction equation
[C:1]([C:5]1[C:6]([N+:17]([O-])=O)=[C:7]([OH:16])[C:8]([OH:15])=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]>CCO.[Pd]>[C:1]([C:5]1[C:6]([NH2:17])=[C:7]([OH:16])[C:8]([OH:15])=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 179696104,6-Di-tert-butyl-3-nitrobenzene-1,2-diol

Product 1

HCID 574702513-Amino-4,6-di-tert-butyl-benzene-1,2-diolYield 33%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent

Procedure

To a solution of 4,6-di-tert-butyl-3-nitrobenzene-1,2-diol (1.92 g, 7.2 mmol) in EtOH (70 mL) was added Pd-5% wt. on carbon (200 mg). The mixture was stirred under H2 (1 atm) for 2 h. The reaction was recharged with Pd-5% wt. on carbon (200 mg) and stirred under H2 (1 atm) for another 2 h. The mixture was filtered through Celite and the filtrate was concentrated and purified by column chromatography (10-40% ethyl acetate-hexanes) to give 4,6-di-tert-butyl-3-aminobenzene-1,2-diol (C-26) (560 mg, 33%). 1H NMR (400 MHz, CDCl3) δ 7.28 (s, 1H), 1.42 (s, 9H), 1.38 (s, 9H).

Workup

  1. stirringstirred under H2 (1 atm) for another 2 h
  2. filtrationThe mixture was filtered through Celite
  3. concentrationthe filtrate was concentrated
  4. custompurified by column chromatography (10-40% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-18605130136243a5ae14a175625316b5
Source dataset
uspto-grants-2014_06
Patent number
US08741925B2

Reaction notes

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