Aluminium lithium hydride → HCID 22048374, compound

HRID 1833123Notes

Reaction equation

HRID 1833123 reaction equation
[F:1][C:2]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][C:3]=1[CH2:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([O:17][CH3:18])=[C:12]([O:15][CH3:16])[CH:13]=2)[C:8]([C:19](OCC)=[O:20])=[CH:7][N:6]=1.FC1C=CC(OC)=CC=1C(C1C2C(=CC(OC)=C(OC)C=2)C(C(O)=O)=CN=1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[F:1][C:2]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][C:3]=1[CH2:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([O:17][CH3:18])=[C:12]([O:15][CH3:16])[CH:13]=2)[C:8]([CH2:19][OH:20])=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 21226445Aluminium lithium hydrideHCID 22048390HCID 22048390, compoundHCID 22048421HCID 22048421, compound

Product 1

HCID 22048374HCID 22048374, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The 1-(2-fluoro-5-methoxybenzyl)-4-ethoxycarbonyl-6,7-dimethoxyisoquinoline (4.0 g, 10 mmol, intermediate for 1-(2-Fluoro-5-methoxy-benzoyl)-6,7-dimethoxy-isoquinoline-4-carboxylic acid (Example 26) was dissolved in 60 ml of THF. At 0° C., lithium aluminum hydride (371 mg, 1.0 eq) was added and the mixture was stirred at room temperature overnight. TLC showed complete disappearance of the starting material. The mixture was evaporated to remove solvents and the residue was extracted with methylene chloride and saturated ammonium chloride solution. The organic layer was washed with water and brine. After the evaporation of solvents a solid was obtained. The solid was washed with dry ether and hexane to give 1-(2-fluoro-5-methoxybenzyl)-4-hydroxymethyl-6,7-dimethoxyisoquinoline (3.12 g, 87%).

Workup

  1. customThe mixture was evaporated
  2. customto remove solvents
  3. extractionthe residue was extracted with methylene chloride and saturated ammonium chloride solution
  4. washThe organic layer was washed with water and brine
  5. customAfter the evaporation of solvents a solid
  6. customwas obtained
  7. washThe solid was washed with dry ether and hexane

Sources & evidence

ORD record
ord-88b86fb7c240416cb0ad3a8fff568e52
Source dataset
uspto-grants-2006_06
Patent number
US07067529B2

Reaction notes

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