2-Nitroresorcinol ditosylate → 2-Aminoresorcinol ditosylate

HRID 647224Notes

Reaction equation

HRID 647224 reaction equation
[S:1]([O:11][C:12]1[CH:28]=[CH:27][CH:26]=[C:14]([O:15][S:16]([C:19]2[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[C:13]=1[N+:29]([O-])=O)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[H][H]>C1COCC1.[Ni]>[S:1]([O:11][C:12]1[CH:28]=[CH:27][CH:26]=[C:14]([O:15][S:16]([C:19]2[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[C:13]=1[NH2:29])([C:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[CH:9][CH:10]=1)(=[O:3])=[O:2]

Participants

5

Reactant 2

HCID 543037482-Nitroresorcinol ditosylateHCID 178418361HCID 178418361, compound

Product 1

HCID 867032532-Aminoresorcinol ditosylate

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To 2-nitroresorcinol ditosylate (46.3 g, 0.1 mole) dissolved in THF (650 ml) was added 5 g of Raney Nickel. The reaction was then placed on the Parr-shaker apparatus and hydrogenated at 40 psi. After four hours, the reaction had consumed all of the hydrogen (12 psi, 0.3 mole). The catalyst was removed by filtration and the solvent evaporated under reduced pressure at 40° C. A white crystalline solid was recovered (42.0 g, 97.0 percent). TLC showed the product to be pure.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent evaporated under reduced pressure at 40° C
  3. customA white crystalline solid was recovered (42.0 g, 97.0 percent)

Sources & evidence

ORD record
ord-92fe85bc9a694b218df2981c280649a0
Source dataset
uspto-grants-1983_10
Patent number
US04407930

Reaction notes

Loading…