Hydrochloric Acid → HCID 70155280, compound

HRID 2227510Notes

Reaction equation

HRID 2227510 reaction equation
[C:1]1([C:7]([C:19]2[CH:31]=[CH:30][C:22]([O:23][CH2:24][C:25]([O:27]CC)=[O:26])=[CH:21][CH:20]=2)=[CH:8][C:9](=[O:18])[NH:10][CH2:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CO>[C:1]1([C:7]([C:19]2[CH:31]=[CH:30][C:22]([O:23][CH2:24][C:25]([OH:27])=[O:26])=[CH:21][CH:20]=2)=[CH:8][C:9](=[O:18])[NH:10][CH2:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 86758307HCID 86758307, compound

Product 1

HCID 70155280HCID 70155280, compoundYield 86.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

100 mg of ethyl [4-[1-phenyl-2-[N-(3-pyridylmethyl)carbamoyl]ethenyl]phenoxy]acetate was mixed with 66 mg of potassium carbonate and 10 ml of 50% aqueous methanol, and then refluxed for 2 hours. The reaction mixture was adjusted to pH 6 with 3 mol/l hydrochloric acid, extracted with ethyl acetate, washed twice with water and once with brine, followed by drying over anhydrous magnesium sulfate. The drying agent was filtered off and the solvent was evaporated to give crude crystals (100 mg), which were then recrystallized from ethyl acetate to provide [4-[1-phenyl-2-[-(3-pyridylmethyl)carbamoyl]ethenyl]phenoxy]acetic acid (80 mg, yield: 86.7%) as a white solid.

Workup

  1. temperaturerefluxed for 2 hours
  2. extractionextracted with ethyl acetate
  3. washwashed twice with water and once with brine
  4. dry with materialby drying over anhydrous magnesium sulfate
  5. filtrationThe drying agent was filtered off
  6. customthe solvent was evaporated
  7. customto give crude crystals (100 mg), which
  8. customwere then recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-6046347946e444758ac7ddcf60236347
Source dataset
uspto-grants-2002_07
Patent number
US06413995B1

Reaction notes

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