Aniline → 4-(phenylimino)-2-pentanone

HRID 2301658Notes

Reaction equation

[CH3:1][C:2](=[O:7])[CH2:3][C:4](=O)[CH3:5].[NH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[O-]S([O-])(=O)=O.[Mg+2]>>[C:9]1([N:8]=[C:4]([CH2:3][C:2](=[O:7])[CH3:1])[CH3:5])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

Reactant 3

HCID 6115Aniline

HCID 24083Sulfuric acid magnesium salt (1:1)

HCID 31261Acetylacetone

Product 1

HCID 7787544-(phenylimino)-2-pentanoneYield 70%

Conditions

Temperature: 100 °C

Procedure

500 g of 2,4-pentanedione, 600 g of aniline, and 1000 g of MgSO4 were mixed together at 100° C., and the mixed solution was stirred for 12 hours at 100° C. Then, the solid portion was precipitated, and the liquid portion was recrystallized upon addition of n-pentane to get 605 g of yellow 2-phenylimino-4-pentanone solid (70% yield). From the NMR analysis, the structure was confirmed; 1H-NMR(CDCl3) δ1.98(s, CH3), 2.10(s, CH3), 5.18(s, ═CH), 7.20(m, Ph), 12.6(brs, NH).

Workup

customThen, the solid portion was precipitated
customthe liquid portion was recrystallized upon addition of n-pentane

Sources & evidence

ORD record: ord-7caeea14d5c44077b7785616bd3461fa
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06500906B1

Reaction notes

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