Diethyl 1,4-dihydro-4-(3-benzyloxypyridyl)-2,6-dimethyl-3,5-pyridine dicarboxylate → Diethyl 1,4-dihydro-4-(3-hydroxypyridyl)-2,6-dimethyl-3,5-pyridine dicarboxylate

HRID 1632954Notes

Reaction equation

HRID 1632954 reaction equation
C([O:8][C:9]1[C:10]([CH:15]2[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:19]([CH3:26])[NH:18][C:17]([CH3:27])=[C:16]2[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[N:11][CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1>[Pd].C(O)C>[OH:8][C:9]1[C:10]([CH:15]2[C:16]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[C:17]([CH3:27])[NH:18][C:19]([CH3:26])=[C:20]2[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[N:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 1

HCID 13374596Diethyl 1,4-dihydro-4-(3-benzyloxypyridyl)-2,6-dimethyl-3,5-pyridine dicarboxylate

Product 1

HCID 13374597Diethyl 1,4-dihydro-4-(3-hydroxypyridyl)-2,6-dimethyl-3,5-pyridine dicarboxylateYield 111.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Diethyl 1,4-dihydro-4-(3-benzyloxypyridyl)-2,6-dimethyl-3,5-pyridine dicarboxylate (7.0 grams; 0.016 mole) was hydrogenated in three batches using 1.2 grams of 10% Palladium on carbon. Material was dissolved in 300 ml ethanol and over a period of two hours there was a drop of 44 psi. The reaction mixtures were vacuum filtered through celite and the filtrate concentrated to approximately half the volume. Crystals formed on standing were filtered and collected. Recrystallization from acetonitrile yielded 6.2 grams of yellow crystals, m.p. 238°-239° C.

Workup

  1. customThe reaction mixtures
  2. filtrationfiltered through celite
  3. concentrationthe filtrate concentrated to approximately half the volume
  4. customCrystals formed on standing
  5. filtrationwere filtered
  6. customcollected
  7. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-4eaa762844a44003aa3c379453c95843
Source dataset
uspto-grants-1984_10
Patent number
US04478834

Reaction notes

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