Hydroxylamine → Ciclopirox

HRID 1282728Notes

Reaction equation

HRID 1282728 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.[NH2:15][OH:16]>NC1C=CC=CN=1.NC1C=CC=C(C)N=1>[OH:16][N:15]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

5

Reactant 2

HCID 787HydroxylamineHCID 198583236-Cyclohexyl-4-methyl-2H-pyran-2-one

Product 1

HCID 2749CiclopiroxYield 37%

Reagents, catalysts & solvents 2

HCID 104392-AminopyridineSolventHCID 157652-Amino-6-methylpyridineSolvent

Procedure

2 g of 4-methyl-6-cyclohexyl-2-pyrone and 1 g of hydroxylamine were dissolved in a mixture of 1.5 g of 2-aminopyridine and 4.5 g of 2-amino-6-methylpyridine and stored for 9 days at room temperature. After the usual working up, there were obtained 0.79 g (37 %) of 1-hydroxy-4-methyl-6-cyclohexyl-2-pyridone melting at 143° C.

Sources & evidence

ORD record
ord-fcf4ae0ebc8d4a7cae5a15cda724183c
Source dataset
uspto-grants-1976_08
Patent number
US03972888

Reaction notes

Loading…