4-Hydroxybenzaldehyde → 4-(2-quinolinylmethoxy)Benzaldehyde

HRID 373943Notes

Reaction equation

HRID 373943 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[N:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][C:11]=1[CH2:20]Cl.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[N:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][C:11]=1[CH2:20][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 962WaterHCID 11430Potassium CarbonateHCID 203942-(Chloromethyl)quinoline

Product 1

HCID 145789604-(2-quinolinylmethoxy)Benzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 0.65 g (5.4 mmol) 4-hydroxybenzaldehyde, 0.94 g (5.3 mmol) of 2-quinolinylmethylchloride, and 0.75 g (5.4 mmol) of potassium carbonate in 15 ml of DMF is heated at 60° C. overnight. The reaction mixture is poured into water. The precipitate is collected on a filter and purified by dry column chromatography to give 4(2-quinolinylmethyloxy)benzaldehyde.

Workup

  1. customThe precipitate is collected on
  2. filtrationa filter
  3. custompurified
  4. customby dry column chromatography

Sources & evidence

ORD record
ord-275168e2331340e3906d39c7ad35579c
Source dataset
uspto-grants-1992_11
Patent number
US05166210

Reaction notes

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