3-((4,5-Dichloro-2-nitrophenyl)amino)-1-propanol → 3-[(2-Amino-4,5-dichlorophenyl)amino]-1-propanol hydrochloride

HRID 971730

Reaction equation

HRID 971730 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([NH:9][CH2:10][CH2:11][CH2:12][OH:13])=[C:4]([N+:14]([O-])=O)[CH:3]=1.[H][H]>[Ni].CO>[ClH:1].[NH2:14][C:4]1[CH:3]=[C:2]([Cl:1])[C:7]([Cl:8])=[CH:6][C:5]=1[NH:9][CH2:10][CH2:11][CH2:12][OH:13]

Participants

5

Reactant 2

HCID 1129553-((4,5-Dichloro-2-nitrophenyl)amino)-1-propanolHCID 178418361HCID 178418361, compound

Product 1

HCID 202880583-[(2-Amino-4,5-dichlorophenyl)amino]-1-propanol hydrochloride

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of 39.7 parts of 3-[(4,5-dichloro-2-nitrophenyl)amino]-1-propanol and 400 parts of methanol is hydrogenated at normal pressure and at room temperature with 5 parts of Raney-nickel catalyst. After the calculated amount of hydrogen is taken up, the catalyst is filtered off. The filtrate is acidified with 24 parts of a hydrochloric acid solution while stirring. The solvent is evaporated and the solid residue is stirred in 2-propanol. The product is filtered off and dried in vacuo, yielding 31.5 parts of 3-[(2-amino-4,5-dichlorophenyl)amino]-1-propanol hydrochloride; mp 185° C.

Workup

  1. filtrationthe catalyst is filtered off
  2. customThe solvent is evaporated
  3. stirringthe solid residue is stirred in 2-propanol
  4. filtrationThe product is filtered off
  5. customdried in vacuo

Sources & evidence

ORD record
ord-c0643647303e451ea0d07db215810690
Source dataset
uspto-grants-1979_07
Patent number
US04160836

Linked notes

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