Quinoline → HCID 69417687, compound

HRID 916956Notes

Reaction equation

HRID 916956 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10](C(O)=O)[C:11](=[O:22])[NH:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Cl:21])=[CH:4][CH:3]=1.N1C2C(=CC=CC=2)C=CC=1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11](=[O:22])[NH:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Cl:21])=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 7047QuinolineHCID 69416039HCID 69416039, compound

Product 1

HCID 69417687HCID 69417687, compound

Conditions

Temperature
235 °C

Procedure

An oven-dried round bottom flask equipped with a magnetic stir bar and a reflux condenser was charged with 0.365 g (0.93 mmol) of 5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid from the product of Step A in Example 32 and 5 mL of freshly distilled quinoline. The reaction mixture was stirred and heated to 235° C. under a nitrogen atmosphere for 3 hours then cooled to room temperature. The reaction mixture was partitioned between excess EtOAc and 1N HCl, separated and the organic layer was extracted again twice with 1N HCl. The organic layer was washed with saturated brine, dried (MgSO4), filtered and evaporated in vacuo. The residual amorphous solid was used directly in the next step without further purification.

Workup

  1. customAn oven-dried round bottom flask equipped with a magnetic stir bar and a reflux condenser
  2. temperaturethen cooled to room temperature
  3. customThe reaction mixture was partitioned between excess EtOAc and 1N HCl
  4. customseparated
  5. extractionthe organic layer was extracted again twice with 1N HCl
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customThe residual amorphous solid was used directly in the next step without further purification

Sources & evidence

ORD record
ord-a1af523fb72645cca123ae99962b0071
Source dataset
uspto-grants-2007_09
Patent number
US07271266B2

Reaction notes

Loading…