1-[4-Chloro-2-benzoylphenyl]-3-phthalimidopropyne → 1-[4-Chloro-2-benzoylphenyl]-3-phthalimidopropene

HRID 464932Notes

Reaction equation

HRID 464932 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][CH2:10][N:11]2[C:15](=[O:16])[C:14]3=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]3[C:12]2=[O:21])=[C:4]([C:22](=[O:29])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:3]=1>O1CCCC1.[Pd]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][CH2:10][N:11]2[C:15](=[O:16])[C:14]3=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]3[C:12]2=[O:21])=[C:4]([C:22](=[O:29])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:3]=1

Participants

4

Reactant 1

HCID 128782521-[4-Chloro-2-benzoylphenyl]-3-phthalimidopropyne

Product 1

HCID 539580771-[4-Chloro-2-benzoylphenyl]-3-phthalimidopropene

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2.0 g (5 mmole) of 1-[4-chloro-2-benzoylphenyl]-3-phthalimidopropyne and 0.1 g of prehydrogenated 10% palladium on barium sulfate in 50 ml of tetrahydrofuran was hydrogenated at room temperature and atmospheric pressure until 85 ml of hydrogen was absorbed. The catalyst was removed by filtration and the filtrate was concentrated at reduced pressure to dryness. The residue was crystallized from ether to give a white solid, mp 70°-72° C. Recrystallization from ether gave colorless prisms, mp 70°-72° C.

Workup

  1. customwas hydrogenated at room temperature
  2. customatmospheric pressure until 85 ml of hydrogen was absorbed
  3. customThe catalyst was removed by filtration
  4. concentrationthe filtrate was concentrated at reduced pressure to dryness
  5. customThe residue was crystallized from ether
  6. customto give a white solid, mp 70°-72° C
  7. customRecrystallization from ether
  8. customgave colorless prisms, mp 70°-72° C.

Sources & evidence

ORD record
ord-c0b48c2361d1411fadcd11f98d924cc4
Source dataset
uspto-grants-1985_10
Patent number
US04549988

Reaction notes

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