Chloranil → Methyl 6-(cyclohexen-4-yl)-1-(4-hydroxyphenyl)-4-oxo-1,4-dihydronicotinate

HRID 255665Notes

Reaction equation

[CH:1]1[CH2:6][CH2:5][CH:4]([CH:7]2[CH2:16][C:15](=[O:17])[C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][N:8]2[C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=2)[CH2:3][CH:2]=1.ClC1C(=O)C(Cl)=C(Cl)C(=O)C=1Cl>O1CCOCC1>[CH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[N:8]([C:18]3[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=3)[CH:9]=[C:10]([C:15](=[O:17])[CH:16]=2)[C:11]([O:13][CH3:14])=[O:12])[CH2:3][CH:2]=1

Participants

Conditions

Temperature: 80 °C

Procedure

In 20 ml of dioxane was dissolved 1.0 g of methyl 6-(cyclohexen-4-yl)-1-(4-hydroxyphenyl)-4-oxo-1,4,5,6-tetrahydronicotinate, and the resulting solution was heated to 80° C. To this solution was added dropwise a solution of 0.83 g of 2,3,5,6-tetrachloro-p-benzoquinone in 20 ml of dioxane at 80° C., followed by reaction at the same temperature for 1 hour. After completion of this reaction, the reaction mixture was cooled to room temperature, and the precipitated crystals were collected by filtration and washed with 50 ml of dioxane to obtain 0.7 g of methyl 6-(cyclohexene-4-yl)-1-(4-hydroxyphenyl)-4-oxo-1,4-dihydronicotinate having a melting point of 250° C. or more.

Workup

customfollowed by reaction at the same temperature for 1 hour
customAfter completion of this reaction
temperaturethe reaction mixture was cooled to room temperature
filtrationthe precipitated crystals were collected by filtration
washwashed with 50 ml of dioxane

Sources & evidence

ORD record: ord-415cbe74a1d14afa97ec427c7083b3cd
Source dataset: uspto-grants-1987_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04698352

Reaction notes

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