Sodium Hydroxide → HCID 45273912, compound

HRID 1184526Notes

Reaction equation

HRID 1184526 reaction equation
C([O:4][C:5]1[CH:6]=[C:7](/[CH:13]=[CH:14]/[C:15]([NH:17][C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20][CH:19]=2)=[O:16])[CH:8]=[CH:9][C:10]=1[O:11][CH3:12])(=O)C.[OH-].[Na+]>CO>[OH:4][C:5]1[CH:6]=[C:7](/[CH:13]=[CH:14]/[C:15]([NH:17][C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20][CH:19]=2)=[O:16])[CH:8]=[CH:9][C:10]=1[O:11][CH3:12]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67338067HCID 67338067, compound

Product 1

HCID 45273912HCID 45273912, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of (E)-3-(3-acetoxy-4-methoxy-phenyl)-N-naphthalen-1-yl-acrylamide (254 mg, 0.70 mmol) in a mixture of MeOH (4.5 mL) and 50%w/w aqueous NaOH (74 μL) was heated under stirring for 40 min at the reflux temperature. The mixture was then concentrated under reduced pressure to give a light yellow oil that was taken up and triturated with 4 mL of aqueous HCl 0.5N. After filtration and drying 213 mg of the title (E)-3-(3-hydroxy-4-methoxy-phenyl)-N-naphthalen-1-yl-acrylamide were obtained as a white powder.

Workup

  1. temperaturewas heated
  2. concentrationThe mixture was then concentrated under reduced pressure
  3. customto give a light yellow oil that
  4. customtriturated with 4 mL of aqueous HCl 0.5N
  5. filtrationAfter filtration
  6. dry with materialdrying 213 mg of the title (E)-3-(3-hydroxy-4-methoxy-phenyl)-N-naphthalen-1-yl-acrylamide
  7. customwere obtained as a white powder

Sources & evidence

ORD record
ord-417bc9c23ff94246b9bed9b630a4594c
Source dataset
uspto-grants-2014_03
Patent number
US08669261B2

Reaction notes

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