Water → HCID 178520452, compound

HRID 967753Notes

Reaction equation

HRID 967753 reaction equation
C[N:2]([CH:4]=[N:5][C:6](=[O:15])[CH:7]=[CH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)C.Cl.N[OH:18].[OH-].[Na+].O>C(O)(=O)C>[OH:18][NH:2][CH:4]=[N:5][C:6](=[O:15])[CH:7]=[CH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 3745097N-[(Dimethylamino)methylene]-cinnamamide

Product 1

HCID 178520452HCID 178520452, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
5 °C

Procedure

N-[(Dimethylamino)methylene]-cinnamamide (1.0 g, 5.0 mmol) was added to a solution of hydroxylamine hydrochloride (415 mg, 6.0 mmol) in acetic acid (5 mL of 70% aqueous) and aqueous NaOH (1.2 mL, 5 M, 6.0 mmol). After stirring for 1.5 h water (5 mL) was added, and the reaction mixture was cooled to 5° C. in an ice bath. The solution was partitioned between ethyl acetate and water, and the organics were dried over Na2SO4, then concentrated in vacuo to afford N-[(hydroxyamino)methylene]-cinnamamide (850 mg, 90%). This material was carried on to the next step without further purification.

Workup

  1. additionwas added
  2. customThe solution was partitioned between ethyl acetate and water
  3. dry with materialthe organics were dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8d28f91bda164931a76ed093a67b4430
Source dataset
uspto-grants-2005_10
Patent number
US06956049B1

Reaction notes

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