Aniline → HCID 13580474, compound

HRID 483099Notes

Reaction equation

HRID 483099 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=O.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[H][H]>[Pd].CO>[OH:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH2:4][NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 6115AnilineHCID 956952-Hydroxy-5-methoxybenzaldehydeHCID 178418361HCID 178418361, compound

Product 1

HCID 13580474HCID 13580474, compoundYield 78.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 15.2 g of 2-hydroxy-5-methoxybenzaldehyde, 15 g of aniline and 200 ml of methanol was stirred for 3 hours. The mixture was then hydrogenated at 40 psi in the presence of 2.0 g of 10% Pd/C until 0.1 mole of hydrogen was consumed. The catalyst was removed by filtration and the filtrate was concentrated in vacuo to a yellow oil which was crystallized from ether-n-hexane to yield 18 g of N-(2-hydroxy-5-methoxybenzyl)aniline. M.p. 82.5°-8° C.

Workup

  1. customwas consumed
  2. customThe catalyst was removed by filtration
  3. concentrationthe filtrate was concentrated in vacuo to a yellow oil which
  4. customwas crystallized from ether-n-hexane

Sources & evidence

ORD record
ord-859cb865ff2f412fb237ea6da3f965cd
Source dataset
uspto-grants-1986_03
Patent number
US04578390

Reaction notes

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