Hydroxyamine hydrochloride → Methyl 4-(4-bromophenyl)-4-(hydroxyimino)butanoate

HRID 2188939Notes

Reaction equation

HRID 2188939 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:4][CH:3]=1.[NH2:16][OH:17].Cl.CC(O[Na])=O.C([O-])(O)=O.[Na+]>CO.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[N:16][OH:17])[CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 838865Methyl 4-(4-bromophenyl)-4-oxobutanoateHCID 178418247HCID 178418247, compound

Product 1

HCID 76768798Methyl 4-(4-bromophenyl)-4-(hydroxyimino)butanoateYield 62.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 4-(4-bromophenyl)-4-oxobutanoate (8.0 g, 29 mmol) and NH2OH.HCl (4.8 g, 69 mmol) in MeOH (60 mL) was added a solution of CH3COONa (6.0 g, 73 mmol) in H2O (30 mL) at room temperature. The reaction mixture was heated at reflux for 1 h. The mixture was neutralized with saturated NaHCO3 solution and was extracted with ethyl acetate (50 mL×3). The combined organics were washed with brine, dried over anhydrous Na2SO4, and purified by chromatography on silica gel (3% ethyl acetate in petroleum ether) to afford methyl 4-(4-bromophenyl)-4-(hydroxyimino)butanoate (5.2 g, 62%). 1H NMR (CDCl3, 400 MHz) δ 7.52-7.49 (m, 4H), 3.66 (s, 3H), 3.08 (t, J=8.0, 2H), 2.61 (t, J=8.0, 2H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 1 h
  3. extractionwas extracted with ethyl acetate (50 mL×3)
  4. washThe combined organics were washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. custompurified by chromatography on silica gel (3% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-097bd5dead7a43ad8c88a62cb6a84c5a
Source dataset
uspto-grants-2012_12
Patent number
US08324207B2

Reaction notes

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