Hydrogen Bromide → HCID 19822961, compound

HRID 727998Notes

Reaction equation

HRID 727998 reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][C:23]([O:26]C)=[CH:22][CH:21]=3)=[CH:16][N:15]=2)=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].Br.[OH-].[Na+]>C(O)(=O)C.O>[CH2:1]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=3)=[CH:16][N:15]=2)=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 19822963HCID 19822963, compound

Product 1

HCID 19822961HCID 19822961, compoundYield 68.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Procedure

This 2-(4-heptylphenyl)-5-(4-methyloxyphenyl)pyridine (15 g, 0.042 mol) was dissolved in acetic acid (120 ml), followed by adding a 48% solution of hydrobromic acid (50 ml), refluxing the mixture for 30 hours, cooling the resulting material, pouring it in water, dissolving deposited crystals in 2N-NaOH aqueous solution on heating, adding acetic acid to obtain an acidic solution, filtering off the residue and recrystallizing from EtOH to obtain 2-(4-heptylphenyl)-5-(4-hydroxyphenyl)pyridine (10 g).

Workup

  1. temperaturerefluxing the mixture for 30 hours
  2. temperaturecooling the resulting material
  3. dissolutiondissolving
  4. temperatureon heating
  5. customto obtain an acidic solution
  6. filtrationfiltering off the residue
  7. customrecrystallizing from EtOH

Sources & evidence

ORD record
ord-5eef2242bd7b4765afcb8f9188941498
Source dataset
uspto-grants-1991_09
Patent number
US05047171

Reaction notes

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