Acetic Acid → HCID 69898449, compound

HRID 1884260Notes

Reaction equation

HRID 1884260 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][NH:17][C:18](=[O:29])[C:19]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)=[CH:20][OH:21])=[CH:11][C:10]=1[O:30][CH3:31])C1C=CC=CC=1.Br.C(O)(=O)C>O>[Cl:28][C:25]1[CH:24]=[CH:23][C:22]([C:19](=[CH:20][OH:21])[C:18]([NH:17][CH2:16][CH2:15][C:12]2[CH:13]=[CH:14][C:9]([OH:8])=[C:10]([O:30][CH3:31])[CH:11]=2)=[O:29])=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 69900559HCID 69900559, compound

Product 1

HCID 69898449HCID 69898449, compoundYield 47.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

1.60 g (3.66 mmol) of N-[2-(4-benzyloxy-3-methoxyphenyl)ethyl]-3-hydroxy-2-(4-chlorophenyl)acrylamide, 925 mg (5.49 mmol) of 48% hydrobromic acid and 15 ml of acetic acid were mixed and stirred at 80° C. for 1.5 hours. Water was added to the reaction mixture, which was followed by extracted with ethyl acetate twice, washed with saturated brine twice, dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography (eluent, hexane:ethyl acetate=2:1) to give 600 mg of 2-(4-chlorophenyl)-3-hydroxy-N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]acrylamide.

Workup

  1. extractionby extracted with ethyl acetate twice
  2. washwashed with saturated brine twice
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-37c2906b8e3e488994cd3b788548c5ee
Source dataset
uspto-grants-2004_07
Patent number
US06762321B2

Reaction notes

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