4-Hydroxybenzaldehyde → 4-(2-Methyl-quinolin-4-ylmethoxy)-benzaldehyde

HRID 1245381Notes

Reaction equation

HRID 1245381 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.Cl[CH2:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=[C:14]([CH3:22])[CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.C(OCC)(=O)C>[CH3:22][C:14]1[CH:13]=[C:12]([CH2:11][O:1][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=1

Participants

6

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 115357194-(Chloromethyl)-2-methylquinoline

Product 1

HCID 219111664-(2-Methyl-quinolin-4-ylmethoxy)-benzaldehydeYield 90%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

p-Hydroxybenzaldehyde (3.18 g, 26.1 mmol), 4-chloromethyl-2-methyl-quinoline (5.0 g, 26.1 mmol), and potassium carbonate (7.2 g, 52 mmol) were combined in acetonitrile (100 mL) and heated to reflux overnight. The reaction was allowed to cool to room temperature, diluted with ethyl acetate, filtered to remove the solids, and concentrated to give a semi-solid residue. The crude product was crystallized from ethyl ether to give 4-(2-methyl-quinolin-4-ylmethoxy)-benzaldehyde (6.5 g, 90%) as an off white precipitate. MS found: (M+H)+=278.

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. filtrationfiltered
  4. customto remove the solids
  5. concentrationconcentrated
  6. customto give a semi-solid residue
  7. customThe crude product was crystallized from ethyl ether

Sources & evidence

ORD record
ord-8004bc2841974ee6a4fe0f8d6277fcbf
Source dataset
uspto-grants-2006_10
Patent number
US07125870B2

Reaction notes

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