Water → HCID 178437185, compound

HRID 1174675Notes

Reaction equation

HRID 1174675 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[C:11]([C:14]2[N:15]=[CH:16][N:17](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:18]=2)(O)[CH3:12])[CH:4]=[CH:3][CH:2]=1.O.[OH-].[Na+]>C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1.C(O)(=O)C>[NH:17]1[CH:18]=[C:14]([C:11]([C:9]2[CH:8]=[CH:7][CH:6]=[C:5]3[C:10]=2[N:1]=[CH:2][CH:3]=[CH:4]3)=[CH2:12])[N:15]=[CH:16]1

Participants

7

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 59749567HCID 59749567, compound2×

Product 1

HCID 178437185HCID 178437185, compound

Reagents, catalysts & solvents 3

HCID 6101p-Toluenesulfonic acidCatalystHCID 176Acetic AcidSolventHCID 1140TolueneSolvent

Procedure

1-Quinolin-8-yl-1-(1-trityl-1H-imidazol-4-yl)-ethanol (Intermediate C1) and p-toluenesulfonic acid catalyst in toluene was heated to reflux in a Dean-Stark apparatus for 18 h. The mixture was cooled to rt and freed of solvent. The residue was dissolved in 70% acetic acid:water and heated to 100° C. for 1 h. The reaction mixture was cooled to rt and basified with 2 M NaOH and extracted with chloroform: isopropyl alcohol (3:1). The organic layers were pooled, dried over MgSO4, filtered and concentrated onto silica gel. The product was eluted from a column of silica gel with 4% NH3-MeOH: CH2Cl2 to give 8-[1-(1H-imidazol-4-yl)-vinyl]-quinoline.

Workup

  1. temperatureto reflux in a Dean-Stark apparatus for 18 h
  2. extractionextracted with chloroform: isopropyl alcohol (3:1)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated onto silica gel
  6. washThe product was eluted from a column of silica gel with 4% NH3-MeOH

Sources & evidence

ORD record
ord-fbfcf68f48754e04a72c6117b6721f55
Source dataset
uspto-grants-2010_11
Patent number
US07838545B2

Reaction notes

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