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

HRID 1649737Notes

Reaction equation

HRID 1649737 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:9]1([CH2:14][C:15]([C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[NH:23][C:22](=[O:27])[CH2:21][CH2:20]3)=[O:16])[CH:13]=[CH:12][N:11]=[CH:10]1>CCOCC.O1CCCC1>[OH:16][C:15]([C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[NH:23][C:22](=[O:27])[CH2:21][CH2:20]2)([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH2:14][N:9]1[CH:13]=[CH:12][N:11]=[CH:10]1

Participants

5

Reactant 2

HCID 142072626-(Imidazol-1-ylacetyl)-3,4-dihydrocarbostyrilHCID 178418255HCID 178418255, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 3 ml of 3M phenylmagnesium bromide in ether was added to a suspension of 1.0 g of 6-(imidazol-1-yl acetyl)-3,4-dihydrocarbostyril in 25 ml of tetrahydrofuran at 0° C., the mixture stirred for 30 minutes at 0° C., then at 25° C. for 18 hours. The reaction was quenched with 10 ml of water and extracted with 10% methanol in methylene chloride. The organic extract was washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure to yield a gum which was chromatographed on silica gel, eluting with 5% methanol in methylene chloride, to give 6-[1-hydroxy-1-phenyl-2-(imidazol-1-yl)ethyl]-3,4-dihydrocarbostyril as a foam. 1H NMR (CDCl3) δ2.56 (d, 1H, J=8.1 Hz), 2.58 (d, 1H, J=8.1 Hz), 2.78 (s, 1H), 2.88 (t, 2H, J=8.1 Hz), 4.65 (s, 2H), 6.57 (s, 1H), 6.74 (d, 1H, J=8.82 Hz), 6.77 (s, 1H), 7.14 (m, 2H), 7.25 (s, 1H), 7.30-7.40 (m, 5H), 8.62 (s, 1H).

Workup

  1. waitat 25° C. for 18 hours
  2. customThe reaction was quenched with 10 ml of water
  3. extractionextracted with 10% methanol in methylene chloride
  4. extractionThe organic extract
  5. washwas washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto yield a gum which
  9. customwas chromatographed on silica gel
  10. washeluting with 5% methanol in methylene chloride

Sources & evidence

ORD record
ord-682175909abb4e8fa6cbd1796d4b76ad
Source dataset
uspto-grants-1990_05
Patent number
US04921862

Reaction notes

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