Citric Acid → HCID 57668103, compound

HRID 2191675Notes

Reaction equation

HRID 2191675 reaction equation
I[C:2]1[CH:10]=[C:9]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[N:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][C:26]=2[NH2:28])[CH:21]=[CH:20][CH:19]=1.CN1CCOCC1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[Cu]I.[Cu].O.C(OCC)(=O)C.CN(C)C=O>[O:11]([C:9]1[CH:8]=[CH:7][C:3]([C:4]([OH:6])=[O:5])=[C:2]([NH:28][C:26]2[CH:25]=[CH:24][CH:23]=[C:22]3[C:27]=2[N:18]=[CH:19][CH:20]=[CH:21]3)[CH:10]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

10

Reactant 4

HCID 311Citric AcidHCID 79724-MethylmorpholineHCID 113598-AminoquinolineHCID 57667966HCID 57667966, compound

Product 1

HCID 57668103HCID 57668103, compoundYield 16.3%

Reagents, catalysts & solvents 5

HCID 23978CopperCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To N,N-dimethylformamide 8.8 mL solution of 2-iodo-4-phenoxybenzoic acid 0.88 g were added quinolin-8-amine 0.75 g, N-methylmorpholine 0.85 mL, copper(I) iodide 0.15 g and copper powder 49 mg, and it was stirred at 90° C. for 6 hours and 30 minutes. After the reaction mixture was cooled to room temperature, ethyl acetate and water were added to it, it was adjusted to pH6.5 with 10% citric acid aqueous solution, and insoluble matter was filtrated. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after washing with saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [eluent; hexane:ethyl acetate=2:1] to give 4-phenoxy-2-(quinolin-8-ylamino)benzoic acid 0.15 g of pale yellow solid.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. filtrationwas filtrated
  3. customThe organic layer was separated
  4. washafter washing with saturated sodium chloride aqueous solution
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-d488b13482564bcbb3682ebd9a0a7ef2
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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