HCID 10901360, compound → HCID 9839408, compound

HRID 1457057Notes

Reaction equation

HRID 1457057 reaction equation
[CH3:1][N:2]([CH3:19])[CH:3]1[CH2:18][CH2:17][C:6]2[O:7][C:8]3[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][C:9]=3[C:5]=2[CH2:4]1>C(O)C.[Pt]>[CH3:1][N:2]([CH3:19])[CH:3]1[CH2:18][CH2:17][C:6]2[O:7][C:8]3[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][C:9]=3[C:5]=2[CH2:4]1

Participants

4

Reactant 1

HCID 10901360HCID 10901360, compound

Product 1

HCID 9839408HCID 9839408, compoundYield 78.8%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

A solution of 0.38 gm (1.46 mMol) of N,N-dimethyl-8-nitro-1,2,3,4-tetrahydro-2-dibenzofuranamine in 150 mL of ethanol was hydrogenated over 200 mg of 5% platinum on carbon at 40 p.s.i. for 2 hours at room temperature. The catalyst was removed by filtration and the filtrate concentrated under reduced pressure. The residue was subjected to radial chromatography (silica gel, 2 mm), eluting with 10% methanol (containing about 5% ammonium hydroxide) in chloroform. Fractions containing product were combined and concentrated under reduced pressure to provide 265 mg of N,N-dimethyl-8-amino-1,2,3,4-tetrahydro-2-dibenzofuranamine as a viscous oil. The oil was dissolved in diethyl ether and this solution treated with hydrogen chloride. The precipitated salt was filtered and dried to provide 337 mg (74%) of the title compound.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate concentrated under reduced pressure
  3. washeluting with 10% methanol (containing about 5% ammonium hydroxide) in chloroform
  4. additionFractions containing product
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c78a8e4414e54c9ba289bf98f265d9c8
Source dataset
uspto-grants-1998_12
Patent number
US05846995

Reaction notes

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