Imidazole → 1-hexyl-3-(1H-imidazol-1-ylmethyl)-4-methoxy-6-methyl-2(1H)-quinolinone

HRID 36051Notes

Reaction equation

HRID 36051 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].[CH2:8]([N:14]1[C:23]2[C:18](=[CH:19][C:20]([CH3:24])=[CH:21][CH:22]=2)[C:17]([O:25][CH3:26])=[C:16]([CH2:27]Br)[C:15]1=[O:29])[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]>CN(C)C=O.C(OCC)(=O)C>[CH2:8]([N:14]1[C:23]2[C:18](=[CH:19][C:20]([CH3:24])=[CH:21][CH:22]=2)[C:17]([O:25][CH3:26])=[C:16]([CH2:27][N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)[C:15]1=[O:29])[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 152333491-hexyl-3-bromomethyl-4-methoxy-6-methyl-2(1H)-quinolinone

Product 1

HCID 152333511-hexyl-3-(1H-imidazol-1-ylmethyl)-4-methoxy-6-methyl-2(1H)-quinolinone

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of imidazole (0.07 g) in dimethylformamide (1.5 ml) was stirred with 60% sodium hydride (0.04 g) at ice-bath temperature under nitrogen until the reaction was complete. The reaction mixture was then treated with a solution of 1-hexyl-3-bromomethyl-4-methoxy-6-methyl-2(1H)-quinolinone (Example 14, 0.27 g) in dimethylformamide (3 ml) and stirred at room temperature for 2 hours. The solution was then diluted with ethyl acetate and washed several times with water. The organic layer was then dried and evaporated under reduced .pressure. The crude reaction product was chromatographed on silica-gel (44 g). Elution with 2% methanoldichloromethane gave 1 -hexyl-3-(1H-imidazol- 1 -ylmethyl)-4-methoxy-6-methyl-2(1H)-quinolinone which crystallized as a white solid. That the expected product was obtained was confirmed by the spectral data: MS: m/e 353 (M+); NMR (CDCl3): δ3.90 (s, 3H, OCH3), 5.18 (s, 2H, CH2 -Im), 6.99, 7.14, 7.72 (s, 3H, CH=) wherein Im represents imidazole.

Workup

  1. washwashed several times with water
  2. customThe organic layer was then dried
  3. customevaporated under reduced .pressure
  4. customThe crude reaction product
  5. customwas chromatographed on silica-gel (44 g)
  6. washElution with 2% methanoldichloromethane

Sources & evidence

ORD record
ord-558e3c4230d3406993632f04942c2115
Source dataset
uspto-grants-1995_05
Patent number
US05412104

Reaction notes

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