Aluminium lithium hydride → HCID 54113030, compound

HRID 482889Notes

Reaction equation

HRID 482889 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C([O:9][C:10]([C:12]1[C:13]([CH3:29])=[N:14][C:15]2[C:16](=[CH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:17][CH2:18][CH2:19][C:20]=2[CH:21]=1)=O)C>C1COCC1>[CH3:29][C:13]1[C:12]([CH2:10][OH:9])=[CH:21][C:20]2[CH2:19][CH2:18][CH2:17][C:16](=[CH:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:15]=2[N:14]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 53964573HCID 53964573, compound

Product 1

HCID 54113030HCID 54113030, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of LiAlH4 (2.81 g) in THF (250 ml) is treated with 5,6,7,8-tetrahydro-2-methyl-8-(phenylmethylene)-3-quinolinecarboxylic acid ethyl ester (7.43 g) and reacted for 25 minutes. Excess reagent is quenched, the mixture is diluted with ethyl acetate and filtered. The filtrate is washed, dried and evaporated to yield crude 5,6,7,8-tetrahydro-2-methyl-8-(phenylmethylene)-3-quinolinemethanol (7.3 g). Crystallization from aqueous ethanol gives 5.10 g of pure 5,6,7,8-tetrahydro-2-methyl-8-(phenylmethylene)-3-quinolinemethanol (m.p. 102° C.-103° C.) as two crops.

Workup

  1. customreacted for 25 minutes
  2. customExcess reagent is quenched
  3. additionthe mixture is diluted with ethyl acetate
  4. filtrationfiltered
  5. washThe filtrate is washed
  6. customdried
  7. customevaporated
  8. customto yield crude 5,6,7,8-tetrahydro-2-methyl-8-(phenylmethylene)-3-quinolinemethanol (7.3 g)
  9. customCrystallization from aqueous ethanol

Sources & evidence

ORD record
ord-6eeb7d88626e4ca19bc7cf19541aca2b
Source dataset
uspto-grants-1986_03
Patent number
US04576949

Reaction notes

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