3-(2-phthalimidoethenyl)-5-ethyl-6-methylpyridin-2(1H)-one → L 693593

HRID 1033019Notes

Reaction equation

HRID 1033019 reaction equation
[C:1]1(=[O:23])[N:5]([CH:6]=[CH:7][C:8]2[C:9](=[O:17])[NH:10][C:11]([CH3:16])=[C:12]([CH2:14][CH3:15])[CH:13]=2)[C:4](=[O:18])[C:3]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:2]12>CO.O1CCCC1.[Pd]>[C:4]1(=[O:18])[N:5]([CH2:6][CH2:7][C:8]2[C:9](=[O:17])[NH:10][C:11]([CH3:16])=[C:12]([CH2:14][CH3:15])[CH:13]=2)[C:1](=[O:23])[C:2]2=[CH:22][CH:21]=[CH:20][CH:19]=[C:3]12

Participants

5

Reactant 1

HCID 4642723-(2-phthalimidoethenyl)-5-ethyl-6-methylpyridin-2(1H)-one

Product 1

HCID 65001L 693593

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A partial suspension of 3-(2-phthalimidoethenyl)-5-ethyl-6-methylpyridin-2(1H)-one (145 mg, 0.47 mmol) in methanol (20 mL) and tetrahydrofuran (20 mL) containing 5% palladium/carbon (117 mg) was hydrogenated at atmospheric pressure for 10-20 hours. The catalyst was filtered off and the solvents evaporated to give product. This material was recrystallized from methanol to yield 110 mg (75%), m.p. 232°-233° C.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvents evaporated
  3. customto give product
  4. customThis material was recrystallized from methanol
  5. customto yield 110 mg (75%), m.p. 232°-233° C.

Sources & evidence

ORD record
ord-9172fd5e92e744e9acb7388c0e29534e
Source dataset
uspto-grants-1994_05
Patent number
US05308854

Reaction notes

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