Hydroxylamine → HCID 58170470, compound

HRID 1619148Notes

Reaction equation

HRID 1619148 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[CH3:16])[C:5](/[N:7]=[C:8](/[N:10](C)C)\[CH3:9])=[O:6].NO.[OH-].[Na+]>O1CCOCC1.C(O)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:5]2[O:6][N:10]=[C:8]([CH3:9])[N:7]=2)[CH:13]=[CH:14][C:15]=1[CH3:16]

Participants

6

Reactant 3

HCID 787HydroxylamineHCID 14798Sodium HydroxideHCID 178464757HCID 178464757, compound

Product 1

HCID 58170470HCID 58170470, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of (E)-3-bromo-N-(1-(dimethylamino)ethylidene)-4-methylbenzamide (preparation 57b, 0.20 g, 0.71 mmol) in dioxane (1.20 mL) was added dropwise to a stirred solution of hydroxylamine (0.06 g, 0.85 mmol) and sodium hydroxide (0.03 g, 0.85 mmol) in acetic acid (2.50 mL) and the mixture was stirred at 100° C. After 0.5 hours, the mixture was concentrated in vacuo, 4% aqueous sodium hydrogen carbonate solution was added to the residue and the mixture was extracted with ethyl acetate. The organic solution was dried (MgSO4) and the solvent removed in vacuo to give the title compound (0.10 g, 56%) as a white solid.

Workup

  1. concentrationthe mixture was concentrated in vacuo, 4% aqueous sodium hydrogen carbonate solution
  2. additionwas added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe organic solution was dried (MgSO4)
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-c4dfe995143245c5b77e9e8076c3f7e5
Source dataset
uspto-grants-2014_07
Patent number
US08772288B2

Reaction notes

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