Deferiprone → 4(1H)-Pyridinone, 1-butyl-3-hydroxy-2-methyl-

HRID 1597123Notes

Reaction equation

HRID 1597123 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)[CH2:12][CH2:13]C>>[CH2:9]([N:4]1[CH:5]=[CH:6][C:7](=[O:8])[C:2]([OH:1])=[C:3]1[CH3:10])[CH2:11][CH2:12][CH3:13]

Participants

3

Reactant 2

HCID 2972DeferiproneHCID 8007Butylamine

Product 1

HCID 1217334(1H)-Pyridinone, 1-butyl-3-hydroxy-2-methyl-

Procedure

A reaction analogous to that used for the synthesis of 3-hydroxy-1,2-dimethyl-4-pyridinone was employed, starting with butylamine (5.3 g). No precipitate was observed after concentration. Recrystallization from ethanol and diethyl ether resulted in a white powder (4.5 g). Proton NMR (D20): 7.84 (d, 1H), 6.80 (d, 1H), 4.15 (q, 2H), 2.39 (s, 3H), 1.61 (m, 2H), 1.16 (m, 2H), 0.72 (t, 3H).

Workup

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

Sources & evidence

ORD record
ord-905fc37a36b34e639f9568ea2782c073
Source dataset
uspto-grants-2001_09
Patent number
US06294152B1

Reaction notes

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