HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 255665
Notes
Print preview

Reaction equation

HRID 255665 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 8371ChloranilHCID 14010724Methyl 6-(cyclohexen-4-yl)-1-(4-hydroxyphenyl)-4-oxo-1,4,5,6-tetrahydronicotinate

Product 1

HCID 14010738Methyl 6-(cyclohexen-4-yl)-1-(4-hydroxyphenyl)-4-oxo-1,4-dihydronicotinateYield 70.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

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

  1. customfollowed by reaction at the same temperature for 1 hour
  2. customAfter completion of this reaction
  3. temperaturethe reaction mixture was cooled to room temperature
  4. filtrationthe precipitated crystals were collected by filtration
  5. 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

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes