Aluminium lithium hydride → HCID 58154805, compound

HRID 2359415Notes

Reaction equation

HRID 2359415 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:4]=[C:5]([C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[C:12]([C:19](O)=[O:20])[CH:13]=[CH:14][CH:15]=3)[N:10]=2)[CH:6]=[CH:7][CH:8]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[F:22][C:2]([F:1])([F:23])[C:3]1[CH:4]=[C:5]([C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[C:12]([CH2:19][OH:20])[CH:13]=[CH:14][CH:15]=3)[N:10]=2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 58154625HCID 58154625, compound

Product 1

HCID 58154805HCID 58154805, compoundYield 48.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(3-(trifluoromethyl)phenyl)quinoline-8-carboxylic acid (1.5 g, 4.72 mmol) in THF (50 ml) was added LiAlH4 (0.36 g, 9.46 mmol) in portions at 0° C. The mixture was stirred at room temperature overnight, quenched with water and concentrated to dryness. The residue was diluted with water and extracted with ethylacetate. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated. Purification by column chromatography (1:10 ethylacetate in pentane) gave the product as a yellow oil (0.69 g, 48% yield).

Workup

  1. customquenched with water
  2. concentrationconcentrated to dryness
  3. additionThe residue was diluted with water
  4. extractionextracted with ethylacetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customPurification by column chromatography (1:10 ethylacetate in pentane)

Sources & evidence

ORD record
ord-aede7ef84fb54becb9edd7138568513c
Source dataset
uspto-grants-2014_04
Patent number
US08685970B2

Reaction notes

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