Piroctone → Ciclopirox

HRID 1861752Notes

Reaction equation

HRID 1861752 reaction equation
ON1C(CC(C)CC(C)(C)C)=CC(C)=CC1=O.[OH:18][N:19]1[C:24]([CH:25]2[CH2:30][CH:29]3C[CH:26]2[CH2:27][CH2:28]3)=[CH:23][C:22]([CH3:32])=[CH:21][C:20]1=[O:33].C1(CCC2C(=O)NC=CC=2)C=CC=CC=1>>[OH:18][N:19]1[C:24]([CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)=[CH:23][C:22]([CH3:32])=[CH:21][C:20]1=[O:33]

Participants

4

Reactant 3

HCID 50259PiroctoneHCID 2680343-(2-phenylethyl)pyridin-2(1h)-oneHCID 22223091HCID 22223091, compound

Product 1

HCID 2749Ciclopirox

Procedure

1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-2-pyridone, 1-hydroxy-4-methyl-6-n-hexyl, -6-iso-hexyl-, 6-n-heptyl- or -6-isoheptyl-2-pyridone, 1-hydroxy-4-methyl-6-octyl- or -6-isooctyl-2-pyridone, in particular 1-hydroxy-4-methyl-6-cyclohexylmethyl- or 6-cyclohexylethyl-2-pyridone, it being possible for the cyclohexyl radical in each case also to carry a methyl radical, 1-hydroxy-4-methyl-6-(2-bicyclo[2,2,1]heptyl)-2-pyridone, 1-hydroxy-3,4-dimethyl-6-benzyl- or -6-dimethylbenzyl-2-pyridone or 1-hydroxy-4-methyl-6-(β-phenylethyl-2-pyridone.

Sources & evidence

ORD record
ord-e1cd9d0c3d044f60aab22cb8cb6b59bb
Source dataset
uspto-grants-2003_03
Patent number
US06534528B1

Reaction notes

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