Hydrochloric Acid → HCID 57668013, compound

HRID 2191673Notes

Reaction equation

HRID 2191673 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].[Cl:18][C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=1.CN1CCOCC1.Cl>[Cu].C(OCC)(=O)C.CN(C)C=O>[Cl:18][C:19]1[CH:25]=[CH:24][C:22]([NH:23][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])=[CH:21][CH:20]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 78124-ChloroanilineHCID 79724-MethylmorpholineHCID 57667966HCID 57667966, compound

Product 1

HCID 57668013HCID 57668013, compoundYield 20%

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
180 °C

Procedure

To N,N-dimethylformamide 0.9 mL solution of 2-iodo-4-phenoxybenzoic acid 45 mg were added 4-chloroaniline 27 mg, copper powder 5 mg and N-methylmorpholine 0.036 mL, and it was stirred under application of pressure at 180° C. for 15 minutes. After the reaction mixture was cooled to room temperature, 1.0 mol/L hydrochloric acid 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 reversed-phase silica gel column chromatography [eluent; 65-100% acetonitrile/0.1% trifluoroacetic acid aqueous solution] to give 2-(4-chloroanilino)-4-phenoxybenzoic acid 9 mg of white solid.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. customThe organic layer was separated
  3. customcollected
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-1d230ba89e3946abab265d124ed4bfae
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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