Acetone → Deferiprone

HRID 273666

Reaction equation

HRID 273666 reaction equation
[CH3:1][C:2]1O[CH:7]=[CH:6][C:4](=[O:5])[C:3]=1[OH:9].CC(C)=O.[CH3:14][NH2:15]>O>[CH3:14][N:15]1[CH:7]=[CH:6][C:4](=[O:5])[C:3]([OH:9])=[C:2]1[CH3:1]

Participants

5

Reactant 3

HCID 180AcetoneHCID 6329MethylamineHCID 8369Maltol

Product 1

HCID 2972DeferiproneYield 53%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Maltol (i.e. 2-methyl-3-hydroxypyran-4-one) 250 g) was dissolved in 25% aqueous methylamine (750 ml) and water (125 ml). The solution was pumped through the CMR (18 ml/min; 160°-2° C.; 900 kPa) and the hot reaction mixture passed directly into acetone (2.5 liters), cooled in an ice water bath. The crystalline product (146 g; 53% yield) was collected by filtration, and washed with acetone (2×250 ml). The corresponding literature method17 involved 6.5 hours at reflux, followed by laborious work up.

Workup

  1. customwas pumped through the CMR (18 ml/min; 160°-2° C.; 900 kPa)
  2. temperaturecooled in an ice water bath
  3. filtrationThe crystalline product (146 g; 53% yield) was collected by filtration
  4. washwashed with acetone (2×250 ml)
  5. temperatureat reflux

Sources & evidence

ORD record
ord-69d841679ad645cdb75e4b78af585880
Source dataset
uspto-grants-1995_02
Patent number
US05387397

Linked notes

Loading…