1-[4-Chloro-2-benzoylphenyl]-3-phthalimidopropyne → HCID 13556875, compound

HRID 464929Notes

Reaction equation

HRID 464929 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>[Ni].O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][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 13556875HCID 13556875, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2 g (5 mmole) of 1-[4-chloro-2-benzoylphenyl]-3-phthalimidopropyne and 1/2 teaspoonful of Raney nickel in 25 ml of tetrahydrofuran was hydrogenated at room temperature and atmospheric pressure. When 240 ml of hydrogen was absorbed, the catalyst was separated by filtration and the filtrate concentrated at reduced pressure to dryness. The residue was crystallized from a mixture of ether and petroleum to give crude product as a tan solid, mp 94°-97° C. Recrystallization from ether gave pale yellow prisms, mp 98°-99° C.

Workup

  1. customwas hydrogenated at room temperature
  2. customWhen 240 ml of hydrogen was absorbed
  3. customthe catalyst was separated by filtration
  4. concentrationthe filtrate concentrated at reduced pressure to dryness
  5. customThe residue was crystallized from a mixture of ether and petroleum
  6. customto give crude product as a tan solid, mp 94°-97° C
  7. customRecrystallization from ether
  8. customgave pale yellow prisms, mp 98°-99° C.

Sources & evidence

ORD record
ord-5dac1004c7aa4f46a545bfd9442e133f
Source dataset
uspto-grants-1985_10
Patent number
US04549988

Reaction notes

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