Potassium Carbonate → 4-chloro-2-(ethoxymethyl)-1-pent-4-ynyl-1H-imidazo[4,5-c]quinoline

HRID 606053Notes

Reaction equation

HRID 606053 reaction equation
[Cl:1][C:2]1[C:11]([NH:12][C:13](=O)[CH2:14][O:15][CH2:16][CH3:17])=[C:10]([NH:19][CH2:20][CH2:21][CH2:22][C:23]#[CH:24])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C.O>[Cl:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:14][O:15][CH2:16][CH3:17])[N:19]([CH2:20][CH2:21][CH2:22][C:23]#[CH:24])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86247598N-[2-chloro-4-(pent-4-ynylamino)quinolin-3-yl]-2-ethoxyacetamide

Product 1

HCID 866168754-chloro-2-(ethoxymethyl)-1-pent-4-ynyl-1H-imidazo[4,5-c]quinoline

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

A solution of N-[2-chloro-4-(pent-4-ynylamino)quinolin-3-yl]-2-ethoxyacetamide (10.23 g, 29.58 mmol) and 6 M aqueous potassium carbonate (7.40 mL, 44.4 mmol) in 9:1 ethanol/water (100 mL) was heated at 50° C. for 16 hours. The volatiles were removed under reduced pressure and the resulting slurry was partitioned between ethyl acetate and water. The organic phase was washed with water (2×) and brine (2×), dried over magnesium sulfate, filtered, and concentrated to afford 4-chloro-2-(ethoxymethyl)-1-pent-4-ynyl-1H-imidazo[4,5-c]quinoline as a slightly impure tan solid (9.5 g).

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customthe resulting slurry was partitioned between ethyl acetate and water
  3. washThe organic phase was washed with water (2×) and brine (2×)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-fb5b9b54a4c14f76980821892cd1374f
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

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