Phosphorus oxychloride → Ethyl 6-bromo-4-chloroquinoline-3-carboxylate

HRID 244594Notes

Reaction equation

HRID 244594 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1O)=[CH:13][C:12]([Br:17])=[CH:11][CH:10]=2)=[O:5])[CH3:2].P(Cl)(Cl)([Cl:20])=O>CN(C)C=O>[Br:17][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[C:15]2[Cl:20]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178469501HCID 178469501, compound

Product 1

HCID 2764138Ethyl 6-bromo-4-chloroquinoline-3-carboxylateYield 97.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Suspend 6-bromo-4-hydroxyquinoline-3-carboxylic acid ethyl ester (11 g, 37 mmol) in anhydrous dimethylformamide (148.6 mL) under nitrogen atmosphere. Add phosphoryl chloride (20.7 mL, 222 mmol, 6 eq.) via syringe over 5 minutes and stir vigorously at room temperature for 3 hours. Quench the reaction by pouring the mixture into ice water (1.5 L) and continue stirring until all the ice has melted. Obtain the solid formed by filtration, rinse with water and allow complete drying to afford the titled compound (11.4 g, 94%). MS (ESI) m/z (M+H)+ 314.0, 316.0.

Workup

  1. customQuench
  2. customthe reaction
  3. customObtain the solid
  4. customformed by filtration
  5. washrinse with water
  6. customallow complete drying

Sources & evidence

ORD record
ord-da53a34f624f49c99e857aeb3725b315
Source dataset
uspto-grants-2014_02
Patent number
US08658668B2

Reaction notes

Loading…