HCID 20183830, compound → HCID 14010764, compound

HRID 255671Notes

Reaction equation

HRID 255671 reaction equation
C(OC([NH:11][CH:12]1[CH2:17][CH2:16][CH:15]([C:18]2[N:19]([C:28]3[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][C:29]=3[CH3:35])[CH:20]=[C:21]([C:25](=[O:27])[CH:26]=2)[C:22]([OH:24])=[O:23])[CH2:14][CH2:13]1)=O)C1C=CC=CC=1>O1CCOCC1.O.[C].[Pd]>[NH2:11][CH:12]1[CH2:17][CH2:16][CH:15]([C:18]2[N:19]([C:28]3[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][C:29]=3[CH3:35])[CH:20]=[C:21]([C:25](=[O:27])[CH:26]=2)[C:22]([OH:24])=[O:23])[CH2:14][CH2:13]1

Participants

5

Reactant 1

HCID 20183830HCID 20183830, compound

Product 1

HCID 14010764HCID 14010764, compoundYield 88.1%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

In a mixture of 10 ml of dioxane and 5 ml of water was dissolved 0.15 g of 6-(4-benzyloxycarbonylaminocyclohexyl)-1-(4-hydroxy-2-methylphenyl)-4-oxo-1,4-dihydronicotinic acid, and 0.03 g of 5% by weight palladium carbon was added. The above acid was hydrogenated under atmospheric pressure for 3 hours. The catalyst was removed by filtration and the solvent was then removed by distillation under reduced pressure. To the residue was added 3 ml of diethyl ether, and the precipitated crystals were collected by filtration and washed with 3 ml of diethyl ether to obtain 0.095 g of 6-(4-aminocyclohexyl)-1-(4-hydroxy-2-methylphenyl)-4-oxo-1,4-dihydronicotinic acid having a melting point of 237°-250° C. (decomp.).

Workup

  1. additionwas added
  2. customThe catalyst was removed by filtration
  3. customthe solvent was then removed by distillation under reduced pressure
  4. additionTo the residue was added 3 ml of diethyl ether
  5. filtrationthe precipitated crystals were collected by filtration
  6. washwashed with 3 ml of diethyl ether

Sources & evidence

ORD record
ord-ee79d03026794a778ba52971c83c5e48
Source dataset
uspto-grants-1987_10
Patent number
US04698352

Reaction notes

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