HCID 20239565, compound → HCID 20239571, compound

HRID 364655Notes

Reaction equation

HRID 364655 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([C:6]([C:22]#[CH:23])([OH:21])[C:7]2[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][N:16]([CH2:19][CH3:20])[CH2:17][CH3:18])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[H][H]>[Pd].C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([CH2:22][CH3:23])([OH:21])[C:7]2[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][N:16]([CH2:17][CH3:18])[CH2:19][CH3:20])=[CH:9][CH:8]=2)=[CH:24][CH:25]=1

Participants

5

Reactant 2

HCID 20239565HCID 20239565, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20239571HCID 20239571, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 241BenzeneSolvent

Procedure

17.9 g. of 4-chloro-4'-[2-(diethylamino)ethoxy]-α-ethinyl-benzhydrol are dissolved in 180 ml. of benzene, and the reaction mixture is hydrogenated in the presence of 0.9 g. of a 10% palladium-on-charcoal catalyst. As soon as the uptake of the calculated amount of hydrogen is complete, the catalyst is filtered off, and benzene is distilled off under reduced pressure. The solid residue is crystallized from n-hexane to yield 14.2 g. of the title compound, melting at 50° to 51° C.

Workup

  1. filtrationthe catalyst is filtered off
  2. distillationbenzene is distilled off under reduced pressure
  3. customThe solid residue is crystallized from n-hexane
  4. customto yield 14.2 g

Sources & evidence

ORD record
ord-04e6c5ae08e740d5a687798cfdb99eed
Source dataset
uspto-grants-1986_08
Patent number
US04605672

Reaction notes

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