8-Hydroxyquinoline → HCID 18453166, compound

HRID 1162689Notes

Reaction equation

HRID 1162689 reaction equation
Br[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([F:11])[CH:3]=1.[OH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1.OC1C=CC=C2C=1N=CC=C2.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.O>[F:11][C:4]1[CH:3]=[C:2]([N:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]2=[O:12])[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7]

Participants

7

Reactant 4

HCID 19238-HydroxyquinolineHCID 11430Potassium CarbonateHCID 3026814-Bromo-2-fluorobenzoic acidHCID 178516071HCID 178516071, compound

Product 1

HCID 18453166HCID 18453166, compoundYield 49.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

73.1 To a solution of 10.96 g of 4-bromo-2-fluoro-benzoic acid in 40 ml of DMSO was added subsequently 6.67 g of 2-hydroxypyridine, 1.10 g of 8-hydroxyquinoline, 1.43 g of Cu(I)I and 7.61 g of K2CO3 and the mixture was heated to 150° C. for 18 h. The suspension was diluted with water, filtered, the residue was washed with AcOEt, triturated with MeOH, filtered and dried to give 5.77 g of 2-fluoro-4-(2-oxo-2H-pyridin-1-yl)-benzoic acid. MS: 234.1 (M+H)+

Workup

  1. filtrationfiltered
  2. washthe residue was washed with AcOEt
  3. customtriturated with MeOH
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-efd66e2132de444ebdbbd29bd5a1a6c3
Source dataset
uspto-grants-2010_10
Patent number
US07820699B2

Reaction notes

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