1-(3-CHLOROPROPOXY)-3-NITROBENZENE → 3-(3-Chloropropoxy)aniline

HRID 1168976Notes

Reaction equation

HRID 1168976 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-])=O)[CH:7]=1.[H][H]>C(O)C.[Pd].[Ni]>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([NH2:12])[CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 2

HCID 98558931-(3-CHLOROPROPOXY)-3-NITROBENZENEHCID 178418361HCID 178418361, compound

Product 1

HCID 229897333-(3-Chloropropoxy)aniline

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Under a nitrogen atmosphere, a solution of 1-(3-chloropropoxy)-3-nitrobenzene (7.90 g, 36.64 mmol) in ethanol was added to 10% palladium on carbon in a Parr hydrogenation bottle. The mixture was hydrogenated on a Parr shaker. Because of very little hydrogen uptake, Raney® nickel (50% slurry in water) was carefully added to the reaction mixture and hydrogenation continued. When hydrogenation was complete the mixture was filtered through a mat of Celite® filter aid. The filtrate was concentrated on a rotary evaporator to an oil.

Workup

  1. filtrationwas filtered through a mat of Celite®
  2. filtrationfilter aid
  3. concentrationThe filtrate was concentrated on a rotary evaporator to an oil

Sources & evidence

ORD record
ord-1cd7fd82847340f2935b412891d4d3ba
Source dataset
uspto-grants-2003_09
Patent number
US06627648B1

Reaction notes

Loading…