8-Methyl-6-(2-methyl-1H-imidazol-1-yl)quinolin-2(1H)-one → HCID 14350348, compound

HRID 649550Notes

Reaction equation

HRID 649550 reaction equation
[I:1]C1N(C2C=C3C(=C(C)C=2)NC(=O)C=C3)C(C)=NC=1.[CH3:20][C:21]1[N:22]([C:26]2[CH:27]=[C:28]3[C:33](=[C:34]([CH3:36])[CH:35]=2)[NH:32][C:31](=[O:37])[CH:30]=[CH:29]3)[CH:23]=[CH:24][N:25]=1>>[I:1][C:24]1[N:25]=[C:21]([CH3:20])[N:22]([C:26]2[CH:27]=[C:28]3[C:33](=[C:34]([CH3:36])[CH:35]=2)[NH:32][C:31](=[O:37])[CH:30]=[CH:29]3)[CH:23]=1

Participants

3

Reactant 2

HCID 144503008-Methyl-6-(2-methyl-1H-imidazol-1-yl)quinolin-2(1H)-oneHCID 20141775HCID 20141775, compound

Product 1

HCID 14350348HCID 14350348, compound

Procedure

n-Butyllithium (16.42 cm3 of a 1.55M solution in n-hexane) was added dropwise to a stirred solution of 6-(4,5-di-iodo-2-methylimidazol-1-yl)-8-methyl-2-(1H)-quinolone (5.0 g) in tetrahydrofuran (100 cm3) at -30° under nitrogen. After 30 minutes saturated aqueous ammonium chloride solution (20 cm3) was added, and the mixture was warmed to room temperature. The mixture was then basified with saturated sodium carbonate solution to pH 10 (approximately) and extracted with methanol:ethyl acetate (1:19 by volume, 100 cm3) and then methanol:dichloromethane (1:19 by volume, 2×200 cm3). 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 recrystallised from methanol/ethyl acetate to afford the title compound, (0.87 g), which was shown spectroscopically to be identical to the product of Preparation 4. Also eluted were fractions which when combined and evaporated afforded a solid, (2.28 g), which was shown to be a mixture of the title compound, 6-(5-iodo-2-methylimidazol-1-yl)-8-methyl-2-(1H)-quinolone, and 6-(2-methylimidazol-1-yl)-8-methyl-2-(1H)-quinolone.

Workup

  1. customto be identical to the product of Preparation 4
  2. washAlso eluted
  3. customevaporated
  4. customafforded a solid, (2.28 g), which

Sources & evidence

ORD record
ord-ecc716f0b90547c895fd312d98d92708
Source dataset
uspto-grants-1988_04
Patent number
US04740513

Reaction notes

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