Iodine → HCID 20546976, compound

HRID 2059291Notes

Reaction equation

HRID 2059291 reaction equation
[I:1]I.[C:3]1([C:9]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)([OH:12])[C:10]#[CH:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH-].[Na+]>CO.O>[I:1][C:11]#[C:10][C:9]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)([C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1)[OH:12]

Participants

6

Reactant 3

HCID 807IodineHCID 14798Sodium HydroxideHCID 3126015HCID 3126015, compound

Product 1

HCID 20546976HCID 20546976, compoundYield 79.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

50.8 g (0.2 mol) of iodine were gradually introduced into a suspension of 42 g (0.2 mol) of 3-phenyl-3-pyridin-4-yl-1-propyn-3-ol in 500 ml of methanol at room temperature, while simultaneously adding 80 ml of concentrated sodium hydroxide solution dropwise. An almost clear solution was thereby obtained. After stirring the solution at room temperture for three hours, it was diluted with a large amount of water and the crystals which had separated out were filtered off, washed with water and dried in vacuo. After recrystallization from methanol, 53 g (79.2% of theory) of 1-iodo-3-phenyl-3-pyridin-4-yl-1-propyn-3-ol were obtained as colorless crystals of melting point 175° C. (decomposition).

Workup

  1. customAn almost clear solution was thereby obtained
  2. customthe crystals which had separated out
  3. filtrationwere filtered off
  4. washwashed with water
  5. customdried in vacuo
  6. customAfter recrystallization from methanol

Sources & evidence

ORD record
ord-9bd6c07f0a404211bbf3fbc573c422b7
Source dataset
uspto-grants-1982_03
Patent number
US04322442

Reaction notes

Loading…