HCID 13854121, compound → HCID 13854127, compound

HRID 1789170Notes

Reaction equation

HRID 1789170 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=2)=[N:6][CH:7]=1>CO.[Pd]>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][O:10][C:11]2[CH:12]=[CH:13][C:14]([NH2:17])=[CH:15][CH:16]=2)=[N:6][CH:7]=1

Participants

4

Reactant 1

HCID 13854121HCID 13854121, compound

Product 1

HCID 13854127HCID 13854127, compoundYield 92.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 4-[2-(5-methyl-2-pyridyl)ethoxy]nitrobenzene (15.0 g) in methanol (150 ml) was subjected to catalytic reduction under 1 atmospheric pressure in the presence of 10% Pd-C (50% wet, 2.0 g). The catalyst was filtered off, and the filtrate was concentrated to give 4-[2-(5-methyl-2-pyridyl)ethoxy]aniline as crystals (12.3 g, 92.5%). Recrystallization from ethyl acetate-hexane gave colorless prisms, m.p. 74°-75° C.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-0a9916073337443eb82f4d3e5056bb19
Source dataset
uspto-grants-1987_08
Patent number
US04687777

Reaction notes

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