Deferiprone → 1-Ethyl-2-methyl-3-hydroxypyridin-4-one

HRID 1597122Notes

Reaction equation

HRID 1597122 reaction equation
[OH:1][C:2]1[C:7](=[O:8])[CH:6]=[CH:5][N:4]([CH3:9])[C:3]=1[CH3:10].[CH2:11](N)C>>[CH2:9]([N:4]1[CH:5]=[CH:6][C:7](=[O:8])[C:2]([OH:1])=[C:3]1[CH3:10])[CH3:11]

Participants

3

Reactant 2

HCID 2972DeferiproneHCID 6341Ethylamine

Product 1

HCID 944131-Ethyl-2-methyl-3-hydroxypyridin-4-one

Procedure

A reaction analogous to that used for the synthesis of 3-hydroxy-1,2-dimethyl-4-pyridinone was employed, starting with 70% ethylamine (4.6 g). No precipitate was observed after concentration. Recrystallization from ethanol and diethyl ether resulted in a white powder (4.2 g). Proton NMR (D20): 7.85 (d, 1H), 6.88 (d, 1H), 4.12 (q, 2H), 2.36 (s, 3H), 1.24 (t, 3H).

Workup

  1. customA reaction analogous to
  2. concentrationafter concentration
  3. customRecrystallization from ethanol and diethyl ether

Sources & evidence

ORD record
ord-8ccafc82b50f429398ab95a8a8a32f95
Source dataset
uspto-grants-2001_09
Patent number
US06294152B1

Reaction notes

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