Hydroxyamine hydrochloride → HCID 19980223, compound

HRID 1461235Notes

Reaction equation

HRID 1461235 reaction equation
[CH3:1][C:2]1O[C:6]([CH2:8][OH:9])=[CH:5][C:4](=[O:10])[C:3]=1[O:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1.Cl.[NH2:22][OH:23]>N1C=CC=CC=1>[CH3:1][C:2]1[N:22]([OH:23])[C:6]([CH2:8][OH:9])=[CH:5][C:4](=[O:10])[C:3]=1[O:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 19980215HCID 19980215, compound

Product 1

HCID 19980223HCID 19980223, compoundYield 30.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 4 g of 6-methyl-5-p-methoxybenzyloxy-2-hydroxymethyl-4-pyrone in 50 ml of pyridine was added 5 g of hydroxylamine hydrochloride at room temperature. The mixture was stirred at 70° to 75° C. for 7 hours. After the reaction liquid was concentrated under reduced pressure, the residue was dissolved in 600 ml of chloroform and washed in succession with water and saturated aqueous sodium hydrogencarbonate solution. After drying the chloroform layer over anhydrous magnesium sulfate, the organic phase was dried and concentrated under reduced pressure. The concentrate was separated and purified by flash column chromatography (eluting solution; chloroform: methanol=20:1) using Wako Gel C-300 (manufactured by Wako Pure Chemical Industry Co., Ltd.) (100 g) to give 1.3 g of the title compound.

Workup

  1. customAfter the reaction liquid
  2. concentrationwas concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in 600 ml of chloroform
  4. washwashed in succession with water and saturated aqueous sodium hydrogencarbonate solution
  5. dry with materialAfter drying the chloroform layer over anhydrous magnesium sulfate
  6. customthe organic phase was dried
  7. concentrationconcentrated under reduced pressure
  8. customThe concentrate was separated
  9. custompurified by flash column chromatography (eluting solution; chloroform: methanol=20:1)

Sources & evidence

ORD record
ord-a744cbdf178748c79978a39cca568452
Source dataset
uspto-grants-1991_12
Patent number
US05075299

Reaction notes

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