Hydroxyamine hydrochloride → 4(1H)-Pyridinone, 5-(diphenylMethoxy)-1-hydroxy-2-(hydroxyMethyl)-

HRID 1639406Notes

Reaction equation

HRID 1639406 reaction equation
[CH:1]([O:14][C:15]1[C:16](=[O:23])[CH:17]=[C:18]([CH2:21][OH:22])O[CH:20]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:25][OH:26].O.O.O.C([O-])(=O)C.[Na+]>C(O)C.O>[OH:26][N:25]1[CH:20]=[C:15]([O:14][CH:1]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:16](=[O:23])[CH:17]=[C:18]1[CH2:21][OH:22]

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 14306387HCID 14306387, compoundHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 143063884(1H)-Pyridinone, 5-(diphenylMethoxy)-1-hydroxy-2-(hydroxyMethyl)-Yield 44%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

17.5 g (0.0568 mol) of the product of Step (1) was added and dissolved in a mixture of ethanol (60 ml) and water (60 ml). Then, 39.5 g (0.568 mol) of hydroxylamine hydrochloride and 77.2 g (0.568 mol) of sodium acetate trihydrate were added thereto, and the mixture was reacted at 60° C. for 18 hours under stirring. Formed precipitates were collected by filtration, washed sequentially with water, ethanol and ethyl ether, and then dried to obtain 8.1 g (yield: 44.0%) of the above identified compound.

Workup

  1. customthe mixture was reacted at 60° C. for 18 hours
  2. customFormed
  3. customprecipitates
  4. filtrationwere collected by filtration
  5. washwashed sequentially with water, ethanol and ethyl ether
  6. customdried
  7. customto obtain 8.1 g (yield: 44.0%) of the

Sources & evidence

ORD record
ord-40095468705f4735b3df554d7e509014
Source dataset
uspto-grants-1989_11
Patent number
US04883879

Reaction notes

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