N-Methoxy-N-methylacetamide → HCID 15224432, compound

HRID 396976Notes

Reaction equation

HRID 396976 reaction equation
[CH3:1][C:2]1[N:3]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:4]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N:7]=[CH:6][C:5]=2[N:14]=1.C([N-]C(C)C)(C)C.[Li+].CON(C)[C:30](=[O:32])[CH3:31]>O1CCCC1>[CH3:17][CH:16]([CH3:18])[CH2:15][N:3]1[C:4]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N:7]=[CH:6][C:5]=2[N:14]=[C:2]1[CH2:1][C:30](=[O:32])[CH3:31]

Participants

5

Reactant 3

HCID 537505N-Methoxy-N-methylacetamideHCID 2724682Lithium diisopropylamideHCID 13958376HCID 13958376, compound

Product 1

HCID 15224432HCID 15224432, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

2-Methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline (1 g, 4.2 mmol) was dissolved in anhydrous tetrahydrofuran (20 mL) then cooled to −78° C. A portion of lithium diisopropyl amide (2.8 mL, 4.2 mmol) was added dropwise to the cooled solution. At 10 minutes post addition, N-methoxy-N-methylacetamide (0.45 g, 4.4 mmol), prepared according to the method of T. A. Oster and T. M. Harris, Tetrahedron Letters, 24, 1851 (1983) was added. After 15 minutes the reaction was quenched with water and the resulting precipitate was collected and dried to provide the desired product as a solid. The structure was confirmed by nuclear magnetic resonance spectroscopy.

Workup

  1. customprepared
  2. additionHarris, Tetrahedron Letters, 24, 1851 (1983) was added
  3. customAfter 15 minutes the reaction was quenched with water
  4. customthe resulting precipitate was collected
  5. customdried

Sources & evidence

ORD record
ord-72f3cb80bf0143bfbba9268d0d913d25
Source dataset
uspto-grants-2003_08
Patent number
US06608201B2

Reaction notes

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