2-(Chloromethyl)quinoline → 2-[6-[(Quinolin-2-yl)methoxy]naphthalen-2-yl]propanoic acid

HRID 1087904Notes

Reaction equation

HRID 1087904 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 117258702-[6-[(Quinolin-2-yl)methoxy]naphthalen-2-yl]propanoic acidYield 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-57e12ff646d3459fa2a1f9a2ee37e0cf
Source dataset
uspto-grants-1990_10
Patent number
US04960892

Reaction notes

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