Hydroxyamine hydrochloride → HCID 86754634, compound

HRID 1740310Notes

Reaction equation

HRID 1740310 reaction equation
[CH:1]([C:3]1[CH2:12][CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]=1[C:13]1[CH:14]=[C:15]([CH:20]=[CH:21][CH:22]=1)[C:16]([O:18][CH3:19])=[O:17])=O.Cl.[NH2:24][OH:25].C[O-].[Na+]>CO>[OH:25][N:24]=[CH:1][C:3]1[CH2:12][CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]=1[C:13]1[CH:14]=[C:15]([CH:20]=[CH:21][CH:22]=1)[C:16]([O:18][CH3:19])=[O:17]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 10942334Sodium MethoxideHCID 21838006HCID 21838006, compound

Product 1

HCID 86754634HCID 86754634, compoundYield 77.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 3-(2-formyl-3,4-dihydro-1-naphthyl)benzoate (0.44 g) was added to a mixture of hydroxylamine hydrochloride (0.11 g) and 28 methanolic sodium methoxide (0.31 ml) in methanol (10 ml) and the whole was stirred for 19 hours at ambient temperature. The solvent was removed by concentration. To the residue was added a mixture of ethyl acetate, tetrahydrofuran and water and adjusted to pH 2 with 6N-hydrochloric acid. The separated organic layer was washed with brine, dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was purified by column chromatography on silica gel eluting a mixture of chloroform and methanol (50:1). The eluted fractions containing the desired product were collected and evaporated in vacuo to give methyl 3-(2-hydroxyiminomethyl-3,4-dihydro-1-naphthyl)benzoate (0.36 g).

Workup

  1. customThe solvent was removed by concentration
  2. additionTo the residue was added
  3. additiona mixture of ethyl acetate, tetrahydrofuran and water
  4. washThe separated organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated in vacuo
  7. customthe residue was purified by column chromatography on silica gel eluting
  8. additiona mixture of chloroform and methanol (50:1)
  9. additionThe eluted fractions containing the desired product
  10. customwere collected
  11. customevaporated in vacuo

Sources & evidence

ORD record
ord-15099c93d8e44ee6af89ccaf446eb904
Source dataset
uspto-grants-1999_10
Patent number
US05968985

Reaction notes

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