Hydrochloric Acid → HCID 18473818, compound

HRID 2227504Notes

Reaction equation

HRID 2227504 reaction equation
COC[O:4][C:5]1[CH:10]=[CH:9][C:8](/[C:11](/[CH3:23])=[CH:12]/[C:13]([NH:15][CH2:16][C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)=[O:14])=[CH:7][CH:6]=1.Cl>CO>[OH:4][C:5]1[CH:10]=[CH:9][C:8](/[C:11](/[CH3:23])=[CH:12]/[C:13]([NH:15][CH2:16][C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)=[O:14])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 18473823HCID 18473823, compound

Product 1

HCID 18473818HCID 18473818, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.94 g of (E)-3-[4-(methoxymethoxy)phenyl]-N-(3-pyridylmethyl)-2-buteneamide was dissolved in 38 ml methanol and stirred with 1.9 ml of concentrated hydrochloric acid at room temperature for 8 hours. The reaction mixture was extracted with ethyl acetate and water, and the aqueous layer was further extracted with ethyl acetate. The combined ethyl acetate layers were washed with water and brine, and dried over anhydrous magnesium sulfate. The drying agent was filtered off and the solvent was evaporated to give a residue, which was then recrystallized from ethyl acetate/n-hexane to provide (E)-3-(4-hydroxyphenyl)-N-(3-pyridylmethyl)-2-buteneamide (1.16 g, 96.5% after 2 steps).

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate and water
  2. extractionthe aqueous layer was further extracted with ethyl acetate
  3. washThe combined ethyl acetate layers were washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe drying agent was filtered off
  6. customthe solvent was evaporated
  7. customto give a residue, which
  8. customwas then recrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-8c8f7854825f42879b4f520361a14ff7
Source dataset
uspto-grants-2002_07
Patent number
US06413995B1

Reaction notes

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