2-Nitroresorcinol → 2-Aminoresorcinol

HRID 1377546Notes

Reaction equation

HRID 1377546 reaction equation
[N+:1]([C:4]1[C:10]([OH:11])=[CH:9][CH:8]=[CH:7][C:5]=1[OH:6])([O-])=O>C(O)C.ClCCl.[Pt](=O)=O>[NH2:1][C:4]1[C:10]([OH:11])=[CH:9][CH:8]=[CH:7][C:5]=1[OH:6]

Participants

5

Reactant 1

HCID 117602-Nitroresorcinol

Product 1

HCID 694512-AminoresorcinolYield 95.1%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A suspension of 2-nitroresorcinol (4.995 g) and platinum (IV) oxide (356 mg) in ethanol (90 ml) was hydrogenated, at room temperature, at 100 p.s.i. for 4 hours. The reaction mixture was filtered through celite, the filter cake washed with methanol (50 ml), and the combined filtrate evaporated in-vacuo to yield a brown solid. The solid was suspended in dichloromethane (100 ml) and evaporated to dryness to yield the title compound (3.83 g, 95%) as a brown solid. δH (250 Mhz; d6DMSO) 3.85 (2H,br s,NH2), 6.20 (3H,m,ArH), 8.85 (2H,br s,ArOH).

Workup

  1. customwas hydrogenated, at room temperature, at 100 p.s.i
  2. filtrationThe reaction mixture was filtered through celite
  3. washthe filter cake washed with methanol (50 ml)
  4. customthe combined filtrate evaporated in-vacuo
  5. customto yield a brown solid
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-a03e5c6594b546e0abfd918b2b31b2dd
Source dataset
uspto-grants-1997_09
Patent number
US05665737

Reaction notes

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