HCID 178500768, compound → Methyl 6-(cyclohexen-4-yl)-1-(4-hydroxyphenyl)-4-oxo-1,4,5,6-tetrahydronicotinate

HRID 255664Notes

Reaction equation

HRID 255664 reaction equation
[CH:1]1[CH2:6][CH2:5][CH:4]([CH:7]=[CH:8][C:9](=[O:24])[C:10](=[CH:15][NH:16][C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)[C:11]([O:13][CH3:14])=[O:12])[CH2:3][CH:2]=1>CN(C)C=O>[CH:1]1[CH2:6][CH2:5][CH:4]([CH:7]2[CH2:8][C:9](=[O:24])[C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:15][N:16]2[C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)[CH2:3][CH:2]=1

Participants

3

Reactant 1

HCID 178500768HCID 178500768, compound

Product 1

HCID 14010724Methyl 6-(cyclohexen-4-yl)-1-(4-hydroxyphenyl)-4-oxo-1,4,5,6-tetrahydronicotinateYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 20 ml of N,N-dimethylformamide was dissolved 2.0 g of methyl 5-(cyclohexen-4-yl)-2-(4-hydroxyphenylaminomethylene)-3-oxo-4-pentenoate, and they were reacted at 140° C. for 4 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure, and to the residue was added 50 ml of dioxane, after which the precipitated crystals were collected by filtration and washed with 30 ml of diethyl ether to obtain 1.4 g of methyl 6-(cyclohexen-4-yl)-1-(4-hydroxyphenyl)-4-oxo-1,4,5,6-tetrahydronicotinate having a melting point of 155°-157° C.

Workup

  1. customwere reacted at 140° C. for 4 hours
  2. customAfter completion of the reaction
  3. customthe solvent was removed by distillation under reduced pressure
  4. additionto the residue was added 50 ml of dioxane
  5. filtrationafter which the precipitated crystals were collected by filtration
  6. washwashed with 30 ml of diethyl ether

Sources & evidence

ORD record
ord-552443bc5acc454599975342a96f610b
Source dataset
uspto-grants-1987_10
Patent number
US04698352

Reaction notes

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