3-(Benzyloxy)-1,2-dimethylpyridin-4(1H)-one → Deferiprone

HRID 1904949Notes

Reaction equation

HRID 1904949 reaction equation
[CH3:1][N:2]1[CH:7]=[CH:6][C:5](=[O:8])[C:4]([O:9]CC2C=CC=CC=2)=[C:3]1[CH3:17]>Br>[CH3:1][N:2]1[CH:7]=[CH:6][C:5](=[O:8])[C:4]([OH:9])=[C:3]1[CH3:17]

Participants

3

Reactant 1

HCID 149562813-(Benzyloxy)-1,2-dimethylpyridin-4(1H)-one

Product 1

HCID 2972DeferiproneYield 82.4%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

1,2-Dimethyl-3-benzyloxypyrid-4-one (2 g) is added to concentrated hydrobromic acid (10 ml) and heated in a steam bath for 30 minutes. The resulting mixture is then recrystallised from water to yield 1,2-dimethyl-3-hydroxypyrid-4-one (1 g), m.p. 230° C. (with decomposition); νmax (nujol) 1620, 3150 cm-1 ; δ(d6DMSO) 2.3(s, 3H), 3.8(s, 3H), 6.9(d, 1H), 7.8(d, 1H); M+ 139.

Workup

  1. temperatureheated in a steam bath for 30 minutes
  2. customThe resulting mixture is then recrystallised from water

Sources & evidence

ORD record
ord-40992e21567c4b20bcecab63b4454a51
Source dataset
uspto-grants-1989_06
Patent number
US04840958

Reaction notes

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