HCID 15617183, compound → HCID 15617212, compound

HRID 1709600Notes

Reaction equation

HRID 1709600 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:16]([CH2:17][CH:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[OH:19])[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)=[CH:4][CH:3]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:16]([CH2:17][C:18]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[O:19])[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 15617183HCID 15617183, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 15617212HCID 15617212, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Under nitrogen atmosphere, a solution of 2-(4-chlorophenyl)-α-phenyl-3H-imidazo[4,5-b]pyridine-3-ethanol (9.44 g, 0.027 mole) in methylene chloride (50 ml) was added to a stirred suspension of pyridinium chlorochromate (8.75 g, 0.041 mole) in methylene chloride (100 ml) and allowed to stir at room temperature overnight. The reaction mixture was filtered. The residue was treated with boiling methylene chloride and filtered. The methylene chloride filtrate was treated with Florisil® and filtered. The filtrate was evaporated to dryness and the residue was recrystallized from isopropyl alcohol. The crystals were collected by filtration, washed with isopropyl alcohol/water, and dried under high vacuum overnight at room temperature to give 5.0 g (54%) of title compound, mp. 211°-212.5° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. additionThe residue was treated with boiling methylene chloride
  3. filtrationfiltered
  4. additionThe methylene chloride filtrate was treated with Florisil®
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness
  7. customthe residue was recrystallized from isopropyl alcohol
  8. filtrationThe crystals were collected by filtration
  9. washwashed with isopropyl alcohol/water
  10. customdried under high vacuum overnight at room temperature

Sources & evidence

ORD record
ord-912ce8cc686a4305b67c93539198bf13
Source dataset
uspto-grants-1990_08
Patent number
US04948800

Reaction notes

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