N,N-Dimethylaniline → HCID 15458589, compound

HRID 1604572Notes

Reaction equation

HRID 1604572 reaction equation
[CH3:1][C:2]1[C:11]([CH3:12])=[C:10](O)[C:9]2[C:4](=[C:5]([O:14][CH3:15])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.CN(C)C1C=CC=CC=1.P(Cl)(Cl)([Cl:27])=O>>[Cl:27][C:10]1[C:9]2[C:4](=[C:5]([O:14][CH3:15])[CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]([CH3:1])[C:11]=1[CH3:12]

Participants

4

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 178488806HCID 178488806, compound

Product 1

HCID 15458589HCID 15458589, compound

Procedure

To a suspension of 2,3-dimethyl-4-hydroxy-8-methoxyquinoline (3.0 g) in phosphoryl chloride was dropwise added N,N-dimethylaniline (3.58 g) under ice-cooling, and the mixture was stirred for 15 minutes at the same temperature, for 30 minutes at ambient temperature and then for 1 hour at 70° C. The solvent was removed, and saturated sodium bicarbonate solution and 10% solution of methanol in dichloromethan were added to the residue. The organic layer was dried over magnesium sulfate and concentrated. The residue wa purified by flash chromatography (Ethyl acetatein-hexane=1:2 v/v) to give 4-chloro-2,3-dimethyl-8-methoxyquinoline (3.02 g).

Workup

  1. temperaturecooling
  2. waitfor 1 hour at 70° C
  3. customThe solvent was removed
  4. additionsaturated sodium bicarbonate solution and 10% solution of methanol in dichloromethan were added to the residue
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue wa purified by flash chromatography (Ethyl acetatein-hexane=1:2 v/v)

Sources & evidence

ORD record
ord-4a2074acd3494d64a9be9b3b0a3dccbd
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

Loading…