3-Hydroxybenzaldehyde → HCID 10422857, compound

HRID 1607899Notes

Reaction equation

HRID 1607899 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].Cl.Cl[CH2:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[N:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:21]=[CH:22][C:13]=1[CH2:12][O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6]

Participants

5

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 30838232-(Chloromethyl)quinoline hydrochloride

Product 1

HCID 10422857HCID 10422857, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

With stirring, a mixture of 3-hydroxybenzaldehyde (8.5 g), 2-chloromethylquinoline hydrochloride (17 g), and anhydrous potassium carbonate (100 g) in dimethylformamide (200 ml) was heated for 6 hours. After filtration, the solvent was removed with reduced pressure and the residue was partitioned between chloroform and water. The organic layer was dried and concentrated to an oil which upon cooling and treatment withhexane, gave the product as an off-white colored solid (16 g), m.p. 48°-53° C.

Workup

  1. temperaturewas heated for 6 hours
  2. filtrationAfter filtration
  3. customthe solvent was removed with reduced pressure
  4. customthe residue was partitioned between chloroform and water
  5. customThe organic layer was dried
  6. concentrationconcentrated to an oil which
  7. temperatureupon cooling

Sources & evidence

ORD record
ord-c8d768afa9c8408481381c9e97adae88
Source dataset
uspto-grants-1989_09
Patent number
US04868193

Reaction notes

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