Hydrochloric Acid → HCID 135556085, compound

HRID 2117814Notes

Reaction equation

HRID 2117814 reaction equation
Cl.N1C=CC=CC=1.C[O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[N:21]=[C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[N:23]=2)[CH:19]=[CH:18][CH:17]=1.[OH-].[Na+]>O>[C:28]1([C:24]2[N:23]=[C:22]([C:20]3[CH:19]=[CH:18][CH:17]=[C:16]([C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=4[OH:9])[N:21]=3)[CH:27]=[CH:26][CH:25]=2)[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 14798Sodium HydroxideHCID 23135803HCID 23135803, compound

Product 1

HCID 135556085HCID 135556085, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

Hydrochloric acid (14.8 ml, 177.2 mmol) was added to pyridine (14.3 ml, 177.2 mmol), and the mixture was heated with removing water till an internal reaction temperature reach to 180° C. After the reaction mixture was cooled to 120° C., 6-(2-methoxyphenyl)-6′-phenyl-2,2′-bipyridine (3.0 g, 8.9 mmol) obtained by Example 13 was added to the reaction mixture and stirred for at 180° C. for 2 hours. After the reaction mixture was cooled, to which was then added an aqueous 1 mol/L sodium hydroxide solution, the mixture was extracted with dichloromethane, the solvent was distilled off, and the residue was purified by silica gel column chromatography and recrystallization, thereby obtaining 2.7 g of 2-(6′-phenyl-2,2′-bipyridine-6-yl)phenol as yellow crystal. Yield: 93.9%.

Workup

  1. temperatureAfter the reaction mixture was cooled, to which
  2. extractionthe mixture was extracted with dichloromethane
  3. distillationthe solvent was distilled off
  4. customthe residue was purified by silica gel column chromatography and recrystallization

Sources & evidence

ORD record
ord-d27bba9111bd4c16b6712a2085cb94cc
Source dataset
uspto-grants-2008_10
Patent number
US07442797B2

Reaction notes

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