Hydroxyamine hydrochloride → HCID 73472310, compound

HRID 1003966Notes

Reaction equation

HRID 1003966 reaction equation
Cl.[NH2:2][OH:3].O=[C:5]([C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1)[C:6]([O:8][CH3:9])=[O:7]>CO>[OH:3][N:2]=[C:5]([C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1)[C:6]([O:8][CH3:9])=[O:7]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 12585532Methyl α-oxo-1-naphthaleneacetate

Product 1

HCID 73472310HCID 73472310, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Hydroxylamine hydrochloride (834 mg) was added to a stirred solution of methyl 2-oxo-2-(1-naphthyl)acetate (1.72 g) in methanol. The mixture was left overnight then the solvent was evaporated and the residue partitioned between ethyl acetate and water. The organic phase was washed with water and brine, dried over magnesium sulphate and evaporated. The title oxime (828 mg) was obtained by recrystallisation of the residue from ethyl acetate/hexane. (Found: M+ 229.0743. C13H11NO3 requires 229.0739). νmax (CHCl3) 3311, 1725. δH (250 MHz, CDCl3), 3.84 (3H, s), 7.43 (1H, dd, J 1.21 and 7.12), 7.46-7.64 (4H, m), 7.89-7.97 (2H, m); m/z (EI) 229 (M+).

Workup

  1. customthe solvent was evaporated
  2. customthe residue partitioned between ethyl acetate and water
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried over magnesium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-3e23add7363e421fa2d117bf8d2698d1
Source dataset
uspto-grants-2000_04
Patent number
US06048852

Reaction notes

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