Methanol → 6-(Cyclohexen-4-yl)-1-(4-hydroxyphenyl)-4-oxo-1,4-dihydronicotinic acid

HRID 255666Notes

Reaction equation

HRID 255666 reaction equation
CO.[OH-].[Na+].[CH:5]1[CH2:10][CH2:9][CH:8]([C:11]2[N:12]([C:22]3[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=3)[CH:13]=[C:14]([C:19](=[O:21])[CH:20]=2)[C:15]([O:17]C)=[O:16])[CH2:7][CH:6]=1>C(O)(=O)C>[CH:5]1[CH2:10][CH2:9][CH:8]([C:11]2[N:12]([C:22]3[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=3)[CH:13]=[C:14]([C:19](=[O:21])[CH:20]=2)[C:15]([OH:17])=[O:16])[CH2:7][CH:6]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 14010738Methyl 6-(cyclohexen-4-yl)-1-(4-hydroxyphenyl)-4-oxo-1,4-dihydronicotinate

Product 1

HCID 201838406-(Cyclohexen-4-yl)-1-(4-hydroxyphenyl)-4-oxo-1,4-dihydronicotinic acidYield 73.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In a mixture consisting of 5 ml of methanol and 5 ml of a 1N aqueous sodium hydroxide solution was dissolved 0.5 g of methyl 6-(cyclohexen-4-yl)-1-(4-hydroxyphenyl)-4-oxo-1,4-dihydronicotinate, and they wre reacted at room temperature for 30 minutes. After completion of the reaction, the reaction mixture was adjusted to a pH of 5.5 with acetic acid, and the precipitated crystals were collected by filtration, washed with 30 ml of water, and dried to obtain 0.35 g of 6-(cyclohexen-4-yl)-1-(4-hydroxyphenyl)-4-oxo-1,4-dihydronicotinic acid having a melting point of 250° C. or more.

Workup

  1. customwre reacted at room temperature for 30 minutes
  2. customAfter completion of the reaction
  3. filtrationthe precipitated crystals were collected by filtration
  4. washwashed with 30 ml of water
  5. customdried

Sources & evidence

ORD record
ord-700c094de41842f59350ba76a793a0e2
Source dataset
uspto-grants-1987_10
Patent number
US04698352

Reaction notes

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