Water → HCID 19867092, compound

HRID 649546Notes

Reaction equation

HRID 649546 reaction equation
C([Li])CCC.Cl[C:7]1[N:11]([C:12]2[CH:13]=[C:14]3[C:19](=[C:20]([CH3:22])[CH:21]=2)[NH:18][C:17](=[O:23])[CH:16]=[CH:15]3)[C:10]([CH3:24])=[N:9][C:8]=1[C:25]#[N:26].[Cl-].[NH4+].O>CCCCCC.O1CCCC1.C(OCC)(=O)C.CO>[C:25]([C:8]1[N:9]=[C:10]([CH3:24])[N:11]([C:12]2[CH:13]=[C:14]3[C:19](=[C:20]([CH3:22])[CH:21]=2)[NH:18][C:17](=[O:23])[CH:16]=[CH:15]3)[CH:7]=1)#[N:26]

Participants

8

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 20141776HCID 20141776, compoundHCID 178418339Butyllithium

Product 1

HCID 19867092HCID 19867092, compoundYield 22.5%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 21584119Ethylacetate methanolSolvent

Procedure

n-Butyllithium (17.5 cm3 of a 1.5M solution in n-hexane) was added dropwise to a stirred solution of 6-(5-chloro-4-cyano-2-methylimidazol-1-yl)-8-methyl-2-(1H)-quinolone (3.57 g) in tetrahydrofuran (THF) (100 cm3) at -70° under nitrogen. After 15 minutes saturated aqueous ammonium chloride solution (20 cm3) was added and the mixture was warmed to room temperature over 1 hour. The mixture was then poured into water (50 cm3), extracted with ethyl acetate (4×150 cm3), and the combined and dried (MgSO4) organic extracts were evaporated in vacuo to give a residue which was chromatographed on silica (Merck "MK 60.9385" [Trade Mark]). Elution with methanol:dichloromethane, 1:19 by volume, followed by combination and evaporation of the appropriate fractions, gave a solid which was boiled with ethyl acetate/methanol, then filtered and dried to afford the title compound, (0.71 g), which was shown spectroscopically to be identical to the product of Preparation 2.

Workup

  1. extractionextracted with ethyl acetate (4×150 cm3)
  2. dry with materialdried (MgSO4) organic extracts
  3. customwere evaporated in vacuo
  4. customto give a residue which
  5. customwas chromatographed on silica (Merck "MK 60.9385" [Trade Mark])
  6. washElution with methanol
  7. customdichloromethane, 1:19 by volume, followed by combination and evaporation of the appropriate fractions
  8. customgave a solid which
  9. filtrationfiltered
  10. customdried

Sources & evidence

ORD record
ord-31420ba7427a4ee492fe0b35846d7a75
Source dataset
uspto-grants-1988_04
Patent number
US04740513

Reaction notes

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