8-Hydroxyquinoline → HCID 11990427, compound

HRID 1669970Notes

Reaction equation

HRID 1669970 reaction equation
C[O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11](=[O:19])[C:12]1[CH:17]=[CH:16][C:15](I)=[CH:14][CH:13]=1.[F:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1.C(=O)([O-])[O-].[Cs+].[Cs+].OC1C=CC=C2C=1N=CC=C2>CN1CCCC1=O.O.C(O)=O.[Cu]Cl>[F:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][C:15]2[CH:16]=[CH:17][C:12]([C:11]([NH:10][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[C:3]([OH:2])=[O:20])=[O:19])=[CH:13][CH:14]=2)=[CH:24][CH:23]=1

Participants

9

Reactant 4

HCID 19238-HydroxyquinolineHCID 97324-FluorophenolHCID 10796Cesium carbonateHCID 1019269HCID 1019269, compound

Product 1

HCID 11990427HCID 11990427, compoundYield 106.5%

Reagents, catalysts & solvents 4

HCID 62652Cuprous chlorideCatalystHCID 284Formic AcidSolventHCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

To 2-(4-iodo-benzoylamino)-benzoic acid methyl ester [75541-84-3] (50 mg) in 1-methyl-2-pyrrolidinone (1 mL) was added 4-fluorophenol (29.4 mg), copper (I) chloride (6.6 mg), cesium carbonate (85 mg) and 8-hydroxy-chinolin (4.7 mg). The reaction mixture was stirred at 120° C. for 18 hours. After such time, the reaction mixture was allowed to cool down to room temperature, diluted with water, formic acid was added (0.3 mL) and the solution was purified by preparative HPLC to yield 2-[4-(4-fluoro-phenoxy)-benzoylamino]-benzoic acid (49.1 mg). MS (m/e): 332.1 (M−H−, 100%).

Workup

  1. temperatureto cool down to room temperature
  2. additionwas added (0.3 mL)
  3. customthe solution was purified by preparative HPLC

Sources & evidence

ORD record
ord-8428ff121300457983615b953773a301
Source dataset
uspto-grants-2011_08
Patent number
US07989657B2

Reaction notes

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