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

HRID 2092923Notes

Reaction equation

HRID 2092923 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-4b77c6e200914bc0b6114f524b8b5ec8
Source dataset
uspto-grants-2013_05
Patent number
US08440829B2

Reaction notes

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