Acetic Acid → HCID 135967941, compound

HRID 1798808Notes

Reaction equation

HRID 1798808 reaction equation
Cl.NO.[OH-].[Na+].C(O)(=O)C.C[N:11](/[CH:13]=[N:14]/[C:15](=[O:23])[C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)C>O1CCOCC1>[O:23]1[C:15]([C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)=[N:14][CH:13]=[N:11]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 178484335HCID 178484335, compound

Product 1

HCID 135967941HCID 135967941, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of hydroxylamine hydrochloride (354 mg, 5.1 mmol) in an a mixture of aqueous 5N sodium hydroxide solution (1 mL, 5 mmol), acetic acid (10 mL) and dioxane (8.5 mL) was added the N-[(1E)-(dimethylamino)methylene]-4-hydroxybenzamide from step 1 of this Example (815 mg, 4.24 mmol). The reaction was stirred at 90° C. for 3 hrs. Upon cooling to room temperature, the solvent was removed under vacuum and residue was purified by column chromatography on an 80 gram biotage silica gel cartridge eluting with 20-50% ethyl acetate/hexanes (gradient) to give the product as white solid. LRMS calc: 162.0; obs: 163.2 (M+1).

Workup

  1. temperatureUpon cooling to room temperature
  2. customthe solvent was removed under vacuum and residue
  3. customwas purified by column chromatography on an 80 gram biotage silica gel cartridge
  4. washeluting with 20-50% ethyl acetate/hexanes (gradient)

Sources & evidence

ORD record
ord-a1627fe981cc4c7b8f8c4df3dc75b45a
Source dataset
uspto-grants-2013_01
Patent number
US08343990B2

Reaction notes

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