3-[(2-Chloro-6-nitrophenyl)amino]-1-propanol → 3-[(2-Amino-6-chlorophenyl)amino]-1-propanol

HRID 46854Notes

Reaction equation

HRID 46854 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-])=O)[C:3]=1[NH:11][CH2:12][CH2:13][CH2:14][OH:15].[H][H]>[Ni].C(O)C>[NH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[NH:11][CH2:12][CH2:13][CH2:14][OH:15]

Participants

5

Reactant 2

HCID 203855663-[(2-Chloro-6-nitrophenyl)amino]-1-propanolHCID 178418361HCID 178418361, compound

Product 1

HCID 203856203-[(2-Amino-6-chlorophenyl)amino]-1-propanolYield 20%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of 115 parts of 3-[(2-chloro-6-nitrophenyl)amino]-1-propanol and 400 parts of ethanol is hydrogenated at normal pressure and at room temperature with 12 parts of a Raney-nickel catalyst. After the calculated amount of hydrogen is taken up, the catalyst is filtered off and the filtrate is evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and 5% of methanol as eluent. The pure fractions are collected and the eluent is evaporated, yielding 20 parts (20%) of 3-[(2-amino-6-chlorophenyl)amino]-1-propanol as a residue.

Workup

  1. filtrationthe catalyst is filtered off
  2. customthe filtrate is evaporated
  3. customThe residue is purified by column-chromatography over silica gel using
  4. additiona mixture of trichloromethane and 5% of methanol as eluent
  5. customThe pure fractions are collected
  6. customthe eluent is evaporated

Sources & evidence

ORD record
ord-35c78a1a0b434d14a7b940ddae6b1322
Source dataset
uspto-grants-1979_11
Patent number
US04175129

Reaction notes

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