2-(Chloromethyl)quinoline → HCID 11725870, compound

HRID 248177

Reaction equation

HRID 248177 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([CH:12]([CH3:16])[C:13]([OH:15])=[O:14])[CH:6]=[CH:5]2.C[O-].[Na+].Cl[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>CO>[CH3:16][CH:12]([C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([O:1][CH2:21][C:22]3[CH:31]=[CH:30][C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[N:23]=3)[CH:3]=2)[CH:8]=1)[C:13]([OH:15])=[O:14]

Participants

5

Reactant 3

HCID 203942-(Chloromethyl)quinolineHCID 162920DesmethylnaproxenHCID 10942334Sodium Methoxide

Product 1

HCID 11725870HCID 11725870, compoundYield 151.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6-hydroxy-α-methyl-2-naphthaleneacetic acid (10.8 g, 50 mmol) in methanol (100 ml) is added sodium methoxide (100 mmol). After 10 minutes the solvent is removed and replaced with dimethylformamide (250 ml). 2-(Chloromethyl)quinoline (17.8 g, 100 mmol) is then added and the reaction mixture is stirred for 8 days at room temperature. The reaction mixture is partitioned between water and methylene chloride, the organic layer is washed with water and evaporated to yield 27 g of an oil. Recrystallization of this oil twice from acetonitrile gives 10.6 g of white crystals of intermediate ether ester (42% yield, m.p. 106°-108° C.).

Workup

  1. customAfter 10 minutes the solvent is removed
  2. customThe reaction mixture is partitioned between water and methylene chloride
  3. washthe organic layer is washed with water
  4. customevaporated

Sources & evidence

ORD record
ord-aaa6707d54f14cdf803fde042812c2cf
Source dataset
uspto-grants-1993_05
Patent number
US05208344

Linked notes

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