6-[1-Hydroxy-1-phenyl-2-(imidazol-1-yl)ethyl]-3,4-dihydrocarbostyril → 6-[1-Phenyl-2-(imidazol-1-yl)ethenyl]-3,4-dihydrocarbostyril

HRID 1649739Notes

Reaction equation

HRID 1649739 reaction equation
O[C:2]([C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[NH:21][C:20](=[O:25])[CH2:19][CH2:18]2)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:3][N:4]1[CH:8]=[CH:7][N:6]=[CH:5]1>C(O)=O>[C:9]1([C:2]([C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[NH:21][C:20](=[O:25])[CH2:19][CH2:18]3)=[CH:3][N:4]2[CH:8]=[CH:7][N:6]=[CH:5]2)[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

3

Reactant 1

HCID 143732636-[1-Hydroxy-1-phenyl-2-(imidazol-1-yl)ethyl]-3,4-dihydrocarbostyril

Product 1

HCID 536619046-[1-Phenyl-2-(imidazol-1-yl)ethenyl]-3,4-dihydrocarbostyril

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of 600 mg of 6-[1-hydroxy-1-phenyl-2-(imidazol-1-yl)ethyl]-3,4-dihydrocarbostyril in 20 ml of anhydrous formic acid was refluxed for 24 hours. The solvent was removed under reduced pressure and the residue partitioned between 5% methanol in methylene chloride and aqueous potassium carbonate. The organic solution was dried over anhydrous sodium sulfate and the solvent removed under reduced pressure. The residue was chromatographed on silica gel, eluting with 5% methanol in methylene chloride, affording 6-[1-phenyl-2-(imidazol-1-yl)ethenyl]-3,4-dihydrocarbostyril as a mixture of (E) and (Z) isomers. 1H NMR of major isomer (CDCl3) δ2.64 (d, 1H, J=8.0 Hz), 2.65 (d, 1H, J=8.0 Hz), 2.94 (t, 2H, J=8.0 Hz), 6.60 (t, 1H, J=1.33 Hz), 6.77 (d, 1H, J=8.1 Hz), 6.90 (t, 1H, J=1.1 Hz), 6.94-7.40 (series of unresolved multiplets, 9H), 8.50 (s, 1H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue partitioned between 5% methanol in methylene chloride and aqueous potassium carbonate
  3. dry with materialThe organic solution was dried over anhydrous sodium sulfate
  4. customthe solvent removed under reduced pressure
  5. customThe residue was chromatographed on silica gel
  6. washeluting with 5% methanol in methylene chloride

Sources & evidence

ORD record
ord-a60f411fdab04389a94103b9f7fa65f8
Source dataset
uspto-grants-1990_05
Patent number
US04921862

Reaction notes

Loading…