Hydrochloric Acid → HCID 178441387, compound

HRID 612943Notes

Reaction equation

HRID 612943 reaction equation
C([O:3][C:4](=O)[CH:5]([C:10](=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:6]([CH3:9])([CH3:8])[CH3:7])C.C[O-].[Na+].Cl.[NH2:23]O.Cl>CO>[C:6]([C:5]1[C:4]([OH:3])=[N:23][O:17][C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([CH3:9])([CH3:8])[CH3:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 319778ethyl 2-benzoyl-3,3-dimethylbutanoateHCID 443297Hydroxyamine hydrochlorideHCID 10942334Sodium Methoxide2×

Product 1

HCID 178441387HCID 178441387, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
-30 °C

Procedure

2-Benzoyl-3,3-dimethylbutyric acid ethyl ester (2.0 g) was dissolved in methanol (20 ml), and sodium methoxide (28% methanol solution, 1.6 ml) was added dropwise thereto at 5° C. under a nitrogen atmosphere, followed by stirring of the resulting mixture for 10 minutes. The reaction mixture was cooled to -30° C., and a suspension of hydroxylamine hydrochloride (1.1 g) and sodium methoxide (28% methanol solution, 6.2 ml) in methanol (10 ml) was added dropwise to the reaction mixture. The resulting mixture was stirred at the same temperature for 30 minutes, and 6N hydrochloric acid (14 ml) was added to the reaction mixture, followed by stirring of the resulting mixture at 80° C. for one hour. After the reaction, the solvent was evaporated under reduced pressure. After the residue was poured into ice-cold water and extracted with ethyl acetate, the organic layer was washed with a saturated aqueous NaCl solution and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure. The residue was crystallized from isopropyl ether to obtain the title compound (0.35 g, 20%) as colorless crystals.

Workup

  1. customat 5° C.
  2. additionwas added dropwise to the reaction mixture
  3. stirringThe resulting mixture was stirred at the same temperature for 30 minutes
  4. stirringby stirring of the resulting mixture at 80° C. for one hour
  5. customAfter the reaction
  6. customthe solvent was evaporated under reduced pressure
  7. additionAfter the residue was poured into ice-cold water
  8. extractionextracted with ethyl acetate
  9. washthe organic layer was washed with a saturated aqueous NaCl solution
  10. dry with materialdried over anhydrous magnesium sulfate
  11. filtrationAfter filtration
  12. customthe solvent was evaporated under reduced pressure
  13. customThe residue was crystallized from isopropyl ether

Sources & evidence

ORD record
ord-b7fe214c97564f7694b3840fac98162d
Source dataset
uspto-grants-1999_12
Patent number
US06005116

Reaction notes

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