2-Nitroresorcinol → 2-Aminoresorcinol

HRID 842104Notes

Reaction equation

HRID 842104 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

Procedure

2-Nitroresorcinol (4.995 g, 0.032 mol) was suspended in ethanol (90 ml). Platinum(IV) oxide (0.356 g) was added and the mixture was shaken under an atmosphere of hydrogen (pH2 100 psi). After 2.75 hours (pH2 90 psi) the reaction mixture was filtered through celite. The residue was washed with methanol (50 ml) and the combined filtrate and washings were evaporated in vacuo at 30° C. During the course of the evaporation the solution, which was originally pale yellow, darkened considerably. A brown solid was obtained which was suspended in dichloromethane (100 ml) and re-evaporated to dryness. Yield 3.83 g (0.031 mol, 95%).

Workup

  1. filtrationAfter 2.75 hours (pH2 90 psi) the reaction mixture was filtered through celite
  2. washThe residue was washed with methanol (50 ml)
  3. customthe combined filtrate and washings were evaporated in vacuo at 30° C
  4. customDuring the course of the evaporation the solution, which
  5. customA brown solid was obtained which
  6. customre-evaporated to dryness

Sources & evidence

ORD record
ord-22cffd9dd01c479c99521cc2cd700228
Source dataset
uspto-grants-2002_04
Patent number
US06372770B1

Reaction notes

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