Aluminium lithium hydride → (4-Methoxyquinolin-7-yl)methanol

HRID 1591973Notes

Reaction equation

HRID 1591973 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]([C:11]1[CH:20]=[C:19]2[C:14]([C:15]([O:21][CH3:22])=[CH:16][CH:17]=[N:18]2)=[CH:13][CH:12]=1)(OC)=[O:8]>C1COCC1>[CH3:22][O:21][C:15]1[C:14]2[C:19](=[CH:20][C:11]([CH2:7][OH:8])=[CH:12][CH:13]=2)[N:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 671383577-Carbomethoxy-4-methoxyquinoline

Product 1

HCID 67138287(4-Methoxyquinolin-7-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2 mL of 1 M LAH (2 mmol) in 25 mL THF is cooled in an ice bath. 450 mg (2.07 mmol) of the title B compound, 7-carbomethoxy-4-methoxyquinoline suspended in 15 mL THF is added and allowed to stir at RT for 18 h. The mixture is quenched with saturated aqueous Na2SO4, filtered, and the filtrate dried over anhydrous MgSO4, filtered, and solvent removed to give (4-methoxyquinolin-7-yl)-methanol: 1H-NMR (CDCl3) δ 4.04 (3H, s), 4.89 (2H, s), 6.72 (1H, d, J=5.3), 7.51 (1H, d, J=8.5), 8.04 (1H, s), 8.16 (1H, d, J=8.5), 8.72 (1H, d, J=5.3).

Workup

  1. additionis added
  2. customThe mixture is quenched with saturated aqueous Na2SO4
  3. filtrationfiltered
  4. dry with materialthe filtrate dried over anhydrous MgSO4
  5. filtrationfiltered
  6. customsolvent removed

Sources & evidence

ORD record
ord-78b3c0ccce0040eaa6be5a91f0e5f2ad
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

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