Methanol → HCID 14010767, compound

HRID 255672Notes

Reaction equation

HRID 255672 reaction equation
C(O[C:9]([NH:11][CH:12]1[CH2:17][CH2:16][CH:15]([C:18]2[N:19]([C:29]3[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][C:30]=3[CH3:36])[CH:20]=[C:21]([C:26](=[O:28])[CH:27]=2)[C:22]([O:24]C)=[O:23])[CH2:14][CH2:13]1)=O)C1C=CC=CC=1.[CH3:37]O>[C].[Pd]>[CH3:9][N:11]([CH3:37])[CH:12]1[CH2:17][CH2:16][CH:15]([C:18]2[N:19]([C:29]3[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][C:30]=3[CH3:36])[CH:20]=[C:21]([C:26](=[O:28])[CH:27]=2)[C:22]([OH:24])=[O:23])[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 887MethanolHCID 14010742HCID 14010742, compound

Product 1

HCID 14010767HCID 14010767, compound

Reagents, catalysts & solvents 1

HCID 178418390HCID 178418390, compoundCatalyst

Procedure

In 15 ml of methanol was dissolved 0.2 g of methyl 6-(4-benzyloxycarbonylaminocyclohexyl)-1-(4-hydroxy-2-methylphenyl)-4-oxo-1,4-dihydronicotinate, and 0.05 g of 5% by weight palladium carbon was added to the resulting solution, and the above ester was hydrogenated under atmospheric pressure for 1.5 hours. Then, the catalyst was removed by filtration, and the solvent was removed by distillation under reduced pressure. To the residue was added 0.4 g of 37% by weight formalin and 0.1 g of formic acid, and they were reacted at 100° C. for 7.5 hours. After completion of this reaction, the solvent was removed by distillation under reduced pressure, and the residue was purified by a column chromatography (Wako Silica Gel C-200; eluent: chloroform/ethanol (3:1 by volume) mixture) to obtain 0.04 g of 6-(4-dimethylaminocyclohexyl)-1-(4-hydroxy-2-methylphenyl)-4-oxo-1,4-dihydronicotinic acid having a melting point of 207°-215° C.

Workup

  1. additionwas added to the resulting solution
  2. customThen, the catalyst was removed by filtration
  3. customthe solvent was removed by distillation under reduced pressure
  4. additionTo the residue was added 0.4 g of 37% by weight formalin and 0.1 g of formic acid, and they
  5. customwere reacted at 100° C. for 7.5 hours
  6. customAfter completion of this reaction
  7. customthe solvent was removed by distillation under reduced pressure
  8. customthe residue was purified by a column chromatography (Wako Silica Gel C-200; eluent: chloroform/ethanol (3:1 by volume) mixture)

Sources & evidence

ORD record
ord-c6263dea706143f78833fcb441cea0b3
Source dataset
uspto-grants-1987_10
Patent number
US04698352

Reaction notes

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