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Sodium hydride → Methyl 5-[3-(quinolin-2-ylmethoxy)-benzyloxy]-nicotinate

HRID 892186
Notes
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Reaction equation

HRID 892186 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[C:8]([OH:10])[CH:7]=[N:6][CH:5]=1.[H-].[Na+].Cl.Cl[CH2:16][C:17]1[CH:18]=[C:19]([CH:32]=[CH:33][CH:34]=1)[O:20][CH2:21][C:22]1[CH:31]=[CH:30][C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:23]=1.C(=O)(O)[O-].[Na+]>CN(C=O)C.C(OCC)C>[N:23]1[C:24]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:30]=[CH:31][C:22]=1[CH2:21][O:20][C:19]1[CH:18]=[C:17]([CH:34]=[CH:33][CH:32]=1)[CH2:16][O:10][C:8]1[CH:7]=[N:6][CH:5]=[C:4]([CH:9]=1)[C:3]([O:2][CH3:1])=[O:11]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 354317Methyl 5-hydroxypyridine-3-carboxylateHCID 516892Sodium BicarbonateHCID 145017072-(3-Chloromethylphenoxymethyl)quinoline hydrochloride

Product 1

HCID 22241358Methyl 5-[3-(quinolin-2-ylmethoxy)-benzyloxy]-nicotinate

Reagents, catalysts & solvents 2

HCID 3283
Diethyl Ether
Solvent
HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-hydroxy nicotinic acid methyl ester (200 mg, 1.3 mmol) in DMF (3 mL) is added 60% sodium hydride emulsion (50 mg, 1.2 mmol) and this mixture is stirred 30 minutes. The free base of 2-(3-chloromethyl-phenoxymethyl)-quinoline hydrochloride (350 mg, 1.2 mmol, example 49) is prepard by partioning the material between ethyl ether and sodium bicarbonate and drying the organic phase with magnesium sulfate. A solution of this free base in DMF (2 mL) is added to the alcohol and this mixture is stirred at 25° C. for 16 hours. The solvent is removed in vacuo, dichloromethane (10 mL) and water (5 mL) is added, and this mixture is acidified to pH6 with acetic acid. The organic layer is dried over magnesium sulfate and the solvent removed in vacuo. The residue is purified by flash chromatography (silica, 4% methanol in dichloromethane) to give the title compound. MS (ESI) 401 (M+H)+.

Workup

  1. dry with materialdrying the organic phase with magnesium sulfate
  2. additionA solution of this free base in DMF (2 mL) is added to the alcohol
  3. stirringthis mixture is stirred at 25° C. for 16 hours
  4. customThe solvent is removed in vacuo, dichloromethane (10 mL) and water (5 mL)
  5. additionis added
  6. dry with materialThe organic layer is dried over magnesium sulfate
  7. customthe solvent removed in vacuo
  8. customThe residue is purified by flash chromatography (silica, 4% methanol in dichloromethane)

Sources & evidence

ORD record
ord-06173c7532164c0e9d2d49a8d15d8464
Source dataset
uspto-grants-2006_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07005440B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes