Hydroxylamine → Piroctone

HRID 1282727Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[C:6]([CH2:8][CH:9]([CH3:15])[CH2:10][C:11]([CH3:14])([CH3:13])[CH3:12])[O:5][C:4](=O)[CH:3]=1.Cl.[NH2:18][OH:19].NC1C=CC=CN=1.NO>>[OH:19][N:18]1[C:6]([CH2:8][CH:9]([CH3:15])[CH2:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:7][C:2]([CH3:1])=[CH:3][C:4]1=[O:5]

Participants

Reactant 4

HCID 787Hydroxylamine

HCID 104392-Aminopyridine

HCID 443297Hydroxyamine hydrochloride

HCID 189704294-Methyl-6-(2,4,4-trimethylpentyl)-2H-pyran-2-one

Product 1

HCID 50259PiroctoneYield 66.5%

Procedure

10 g of 4-methyl-6-(2,4,4-trimethylpentyl)-2-pyrone, 5 g of hydroxylamine hydrochloride and 20 g of 2-aminopyridine were heated for 26 hours to 70°C, whereupon after 17 hours a further 2 g of hydroxylamine were added. Working up was effected as usual and there were obtained 7.1 g (67 %) of 1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-2-pyridone melting at 108° C (Calc.: 5.9 % N, found 5.9 % N).

Sources & evidence

ORD record: ord-95dca5aeab3d4714980c7ae8157d70d3
Source dataset: uspto-grants-1976_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03972888

Reaction notes

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