Citric Acid → HCID 57667912, compound

HRID 2191674Notes

Reaction equation

HRID 2191674 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].[CH:18]1([NH2:24])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.CN1CCOCC1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[Cu]I.[Cu].C(OCC)(=O)C.CN(C)C=O>[CH:18]1([NH:24][C:2]2[CH:10]=[C:9]([O:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:8]=[CH:7][C:3]=2[C:4]([OH:6])=[O:5])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

9

Reactant 4

HCID 311Citric AcidHCID 7965CyclohexylamineHCID 79724-MethylmorpholineHCID 57667966HCID 57667966, compound

Product 1

HCID 57667912HCID 57667912, compound

Reagents, catalysts & solvents 4

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

Conditions

Temperature
180 °C

Procedure

To N,N-dimethylformamide 1.0 mL solution of 2-iodo-4-phenoxybenzoic acid 40 mg, were added cyclohexylamine 0.027 mL, copper(I) iodide 3 mg, copper powder 3 mg and N-methylmorpholine 0.040 mL, and it was stirred under application of pressure at 180° C. for 15 minutes. After the reaction mixture was cooled to room temperature,10% citric acid aqueous solution and ethyl acetate were added to it. The organic layer was separated and collected,dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [Trikonex company, Flash Tube 2008, eluent; hexane:ethyl acetate:acetic acid=20:10:1] to give 2-(cyclohexylamino)-4-phenoxybenzoic acid 5 mg of white solid.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. customThe organic layer was separated
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-d64b373df8034ed09bd2a1c1cf8b2ee5
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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