Imidazole → Ciclopirox

HRID 1282730Notes

Reaction equation

HRID 1282730 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[O:5][C:4](=O)[CH:3]=1.S(O)(O)(=O)=O.[NH2:20][OH:21].N1C=CN=C1>>[OH:21][N:20]1[C:6]([CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:7][C:2]([CH3:1])=[CH:3][C:4]1=[O:5]

Participants

4

Reactant 3

HCID 795ImidazoleHCID 159255Hydroxylamine, sulfate (1:1)2×HCID 198583236-Cyclohexyl-4-methyl-2H-pyran-2-one

Product 1

HCID 2749CiclopiroxYield 93.3%

Procedure

20 g of 4-methyl-6-cyclohexyl-2-pyrone, 8 g of hydroxylamine sulfate and 50 g of imidazole were heated to 90° C. Further 10 g of hydroxylamine sulfate were added portionwise in the course of 3 hours. After a reaction time of 5 hours, the mixture was worked up. 11.8 g of 1-hydroxy-4-methyl-6-cyclohexyl-2-pyridone melting at 143° C were obtained.

Workup

  1. customAfter a reaction time of 5 hours

Sources & evidence

ORD record
ord-7e54ad5a19da48c1b0ac8ab433db7310
Source dataset
uspto-grants-1976_08
Patent number
US03972888

Reaction notes

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