2-(Chloromethyl)quinoline → 3,4-Dihydro-7-(2-quinolinylmethoxy)-1(2H)-naphthalenone

HRID 543291Notes

Reaction equation

HRID 543291 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][C:11]2=[O:14])=[CH:6][CH:5]=1.Cl[CH2:16][C:17]1[CH:26]=[CH:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=1>CN(C)C=O>[N:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:25]=[CH:26][C:17]=1[CH2:16][O:3][C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][C:11]2=[O:14])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 203942-(Chloromethyl)quinolineHCID 24758Sodium hydrideHCID 5718187-hydroxy-3,4-dihydro-2H-naphthalen-1-one

Product 1

HCID 138511063,4-Dihydro-7-(2-quinolinylmethoxy)-1(2H)-naphthalenoneYield 35%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a slurry of NaH (0.29 g, 12.25 mmol) in 25 mL dimethylformamide under nitrogen at 0° C. is added portionwise 7-hydroxy-1-tetralone (2.0 g, 12.33 mmol) over 5 minutes. After half an hour, 2-(chloromethyl)quinoline (2.2 g, 12.43 mmol) is added in 10 mL dimethylformamide. The ice bath is removed and the reaction mixture is stirred overnight. The solvent is then removed in vacuo and the residue is partitioned between 1N sodium hydroxide and methylene chloride. The organic layer is separated, dried over magnesium sulfate, evaporated down to an oil, and chromatographed on silica gel. Elution with 9-1 methylene chloride/ethyl acetate gives 2.0 g(54%). This material is recrystallized from acetonitrile to afford 1.3 g (35%) of yellow crystals, m.p. 98.5°-101.5° C.

Workup

  1. waitAfter half an hour
  2. customThe ice bath is removed
  3. customThe solvent is then removed in vacuo
  4. customthe residue is partitioned between 1N sodium hydroxide and methylene chloride
  5. customThe organic layer is separated
  6. dry with materialdried over magnesium sulfate
  7. customevaporated down to an oil
  8. customchromatographed on silica gel
  9. washElution with 9-1 methylene chloride/ethyl acetate
  10. customgives 2.0 g(54%)
  11. customThis material is recrystallized from acetonitrile

Sources & evidence

ORD record
ord-8358a345745e45ca954a46d714b49d36
Source dataset
uspto-grants-1987_04
Patent number
US04661596

Reaction notes

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