Sodium Iodide → Methyl 8-(dodecyloxy)quinoline-2-carboxylate

HRID 252477Notes

Reaction equation

HRID 252477 reaction equation
[CH2:1](Br)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[Na+].[I-].[H-].[Na+].[CH3:18][O:19][C:20]([C:22]1[CH:31]=[CH:30][C:29]2[C:24](=[C:25]([OH:32])[CH:26]=[CH:27][CH:28]=2)[N:23]=1)=[O:21]>CN(C=O)C.C(Cl)Cl>[CH3:18][O:19][C:20]([C:22]1[CH:31]=[CH:30][C:29]2[C:24](=[C:25]([O:32][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH:26]=[CH:27][CH:28]=2)[N:23]=1)=[O:21]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 89191-BromododecaneHCID 24758Sodium hydrideHCID 12336161Methyl 8-Hydroxyquinoline-2-Carboxylate

Product 1

HCID 66872454Methyl 8-(dodecyloxy)quinoline-2-carboxylateYield 14%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

In a first step, dodecyl bromide (767 μL, 3.2 mmol), NaI (478 mg, 3.2 mmol) and NaH (76 mg, 3.2 mmol) were added to a solution of 8-hydroxyl-quinoline-2-carboxylic acid methyl ester (2.11 mmol) stirring in DMF (dry, 10 mL), and the red reaction was allowed to stir overnight. The crude material resulting from removal of solvents by rotary evaporation was taken into DCM, washed with water, dried over Na2SO4, and filtered. The resulting solution was evaporated to dryness and the desired intermediate, 8-dodecyloxy-quinoline-2-carboxylic acid methyl ester, was obtained by HPLC (isocratic, 75% acetonitrile, 25% water) yielding 169 mg (about 14% yield). This intermediate was in turn deprotected using LiOH in THF/H2O as described in the method of Example 336 to yield the title compound, which was utilized further without additional purification or characterization.

Workup

  1. customthe red reaction
  2. customThe crude material resulting from removal of solvents by rotary evaporation
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customThe resulting solution was evaporated to dryness

Sources & evidence

ORD record
ord-ebd5ed555b5d43279656f61d7c912a24
Source dataset
uspto-grants-2011_01
Patent number
US07868135B2

Reaction notes

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