3-Hydroxybenzaldehyde → HCID 10422857, compound

HRID 1090074Notes

Reaction equation

HRID 1090074 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].Cl[CH2:11][C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH:5]([C:4]1[CH:3]=[C:2]([CH:9]=[CH:8][CH:7]=1)[O:1][CH2:11][C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=1)=[O:6]

Participants

5

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 203942-(Chloromethyl)quinoline

Product 1

HCID 10422857HCID 10422857, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 3-hydroxybenzaldehyde (6.71 g), 2-(chloromethyl)quinoline (8.88 g) and potassium carbonate (8.28 g) in N,N-dimethylformamide (25 ml) was stirred at 60° C. for 3 hours. The mixture was allowed to cool and concentrated in vacuo. The residue was treated with water. The separated oil was extracted with ethyl acetate. The organic layer was washed with brine, dried, and evaporated to give an oil, which was crystallized from n-hexane to yield 2-[[3-(formyl)phenoxy]methyl]quinoline (12.5 g).

Workup

  1. temperatureto cool
  2. concentrationconcentrated in vacuo
  3. additionThe residue was treated with water
  4. extractionThe separated oil was extracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. customdried
  7. customevaporated
  8. customto give an oil, which
  9. customwas crystallized from n-hexane

Sources & evidence

ORD record
ord-3718601d1fdf410eab5a328e0b8d3e1b
Source dataset
uspto-grants-1992_01
Patent number
US05081126

Reaction notes

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