HCID 12878253, compound → HCID 13556876, compound

HRID 464930Notes

Reaction equation

HRID 464930 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:30])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[F:29])[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:12](=[O:21])[C:13]3=[CH:20][CH:19]=[CH:18][CH:17]=[C:14]3[C:15]2=[O:16])=[C:4]([C:22](=[O:30])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[F:29])[CH:3]=1

Participants

4

Reactant 1

HCID 12878253HCID 12878253, compound

Product 1

HCID 13556876HCID 13556876, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 9.6 g (23 mmole) of 1-[4-chloro-2-(2-fluorobenzoyl)phenyl]-3-phthalimidopropyne and 1 teaspoonful of Raney nickel in 70 ml of tetrahydrofuran was hydrogenated at room temperature and atmospheric pressure. When 1.05 L of hydrogen was absorbed the catalyst was separated by filtration and the filtrate was concentrated at reduced pressure to dryness. The residue crystallized from a mixture of ether and petroleum ether to give the product as a tan solid, mp 98°-99° C.

Workup

  1. customwas hydrogenated at room temperature
  2. customWhen 1.05 L of hydrogen was absorbed the catalyst
  3. customwas separated by filtration
  4. concentrationthe filtrate was concentrated at reduced pressure to dryness
  5. customThe residue crystallized from a mixture of ether and petroleum ether

Sources & evidence

ORD record
ord-3f7b3158b50f4c39b579ab140e71a9ee
Source dataset
uspto-grants-1985_10
Patent number
US04549988

Reaction notes

Loading…