3,4-Dihydro-7-(2-quinolinylmethoxy)-1(2H)-naphthalenone → 1,2,3,4-Tetrahydro-7-(2-quinolinylmethoxy)-1-naphthalenol

HRID 580653Notes

Reaction equation

HRID 580653 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][C:8]=1[CH2:17][O:18][C:19]1[CH:28]=[C:27]2[C:22]([CH2:23][CH2:24][CH2:25][C:26]2=[O:29])=[CH:21][CH:20]=1>O1CCCC1>[N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][C:8]=1[CH2:17][O:18][C:19]1[CH:28]=[C:27]2[C:22]([CH2:23][CH2:24][CH2:25][CH:26]2[OH:29])=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 138511063,4-Dihydro-7-(2-quinolinylmethoxy)-1(2H)-naphthalenoneHCID 21226445Aluminium lithium hydride

Product 1

HCID 138511071,2,3,4-Tetrahydro-7-(2-quinolinylmethoxy)-1-naphthalenolYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.62 g (16.33 mmol) lithium aluminum hydride in 80 mL tetrahydrofuran under nitrogen at 0° C. is added dropwise with stirring a solution of 5.0 g (16.48 mmol) of 3,4-dihydro-7-(2-quinolinylmethoxy)-1(2H)-naphthalenone over 1 minute. The ice bath is removed and after 1 hour the reaction is worked up according to Micovic and Mihailovic1. The crude product is recrystallized from ethylacetate/hexane and affords 3.1 g (62%) of white crystals, m.p. 113°-115° C.

Workup

  1. customThe ice bath is removed and after 1 hour the reaction
  2. customThe crude product is recrystallized from ethylacetate/hexane

Sources & evidence

ORD record
ord-1c12dc78d5774c30b1d02f56315b761c
Source dataset
uspto-grants-1988_06
Patent number
US04754043

Reaction notes

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