N,N-Dimethylaniline → HCID 22113061, compound

HRID 581750Notes

Reaction equation

HRID 581750 reaction equation
[CH2:1]([C:3]1[CH:12]=[C:11](O)[C:10]2[C:5](=[C:6]([O:14][CH3:15])[CH:7]=[CH:8][CH:9]=2)[N:4]=1)[CH3:2].CN(C)C1C=CC=CC=1.P(Cl)(Cl)([Cl:27])=O>>[Cl:27][C:11]1[C:10]2[C:5](=[C:6]([O:14][CH3:15])[CH:7]=[CH:8][CH:9]=2)[N:4]=[C:3]([CH2:1][CH3:2])[CH:12]=1

Participants

4

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 178436852HCID 178436852, compound

Product 1

HCID 22113061HCID 22113061, compound

Procedure

To a solution of 2-ethyl-4-hydroxy-8-methoxyquinoline (9.96 g) in phosphoryl chloride (30 ml) was added N,N-dimethylaniline (12.44 ml) below 8° C. in an ice bath. After 10 minutes the mixture was stirred at ambient temperature for 1.5 hours. The solvent was removed in vacuo. The residue was partitioned into dichloromethane and saturated sodium bicarbonate solution. The organic layer was washed with brine and dried over magnesium sulfate. The organic layer was evaporated in vacuo. The residue was purified by column chromatography (hexane--ethyl acetate) and recrystallized from hexane to give 4-chloro-2-ethyl-8-methoxyquinoline (8.90 g) as crystals. mp: 80-81° C.

Workup

  1. customThe solvent was removed in vacuo
  2. customThe residue was partitioned into dichloromethane and saturated sodium bicarbonate solution
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customThe organic layer was evaporated in vacuo
  6. customThe residue was purified by column chromatography (hexane--ethyl acetate)
  7. customrecrystallized from hexane

Sources & evidence

ORD record
ord-8dff07aa3d6b42bebaac714b347c82af
Source dataset
uspto-grants-1999_07
Patent number
US05922711

Reaction notes

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