Hydroxyamine hydrochloride → HCID 85301016, compound

HRID 847532Notes

Reaction equation

HRID 847532 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:16]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)=O)=[CH:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:5][CH:4]=1.Cl.[NH2:27][OH:28].[Na]>CO.O>[OH:28][N:27]=[C:16]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1)[C:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[CH:10][CH2:11][C:12]([O:14][CH3:15])=[O:13]

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 5360545SodiumHCID 53769085Methyl 4,5-bis(4-methoxyphenyl)-5-oxo-3-pentenoate

Product 1

HCID 85301016HCID 85301016, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A 24.5 g quantity of methyl 4,5-bis(4-methoxyphenyl)-5-oxo-3-pentenoate obtained in Example 1 and 51.5 g of hydroxylamine hydrochloride was refluxed with heating in a mixture of 650 ml of methanol and 72 ml of water for 23 hours. With the progress of reaction at this time, 0.9 equivalent weight of sodium hydrogentarbonate was added in divided portions to the reaction system. On completion of the reaction, the methanol was distilled off at a reduced pressure. The residue was dissolved with water and ethyl acetate, and the organic layer was collected, washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium suliate. The organic layer was concentrated at a reduced pressure, and the residue was subjected to silica gel column chromatography (eluants: ethyl acetate-n-hexane) for separation and purification, affording 23 g (yield 90%) of the above-identified compound as an oily product.

Workup

  1. additionwas added in divided portions to the reaction system
  2. customOn completion of the reaction
  3. distillationthe methanol was distilled off at a reduced pressure
  4. dissolutionThe residue was dissolved with water and ethyl acetate
  5. customthe organic layer was collected
  6. washwashed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous magnesium suliate
  8. concentrationThe organic layer was concentrated at a reduced pressure
  9. customthe residue was subjected to silica gel column chromatography (eluants: ethyl acetate-n-hexane) for separation and purification

Sources & evidence

ORD record
ord-e8d200d2f4f445d18602f5358f1dffbf
Source dataset
uspto-grants-1992_08
Patent number
US05142091

Reaction notes

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