Hydrochloric Acid → 3-Methylisoquinoline-4-carbaldehyde

HRID 1597376Notes

Reaction equation

HRID 1597376 reaction equation
[Li]CCCC.Br[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[N:9][C:8]=1[CH3:17].CN([CH:21]=[O:22])C.Cl.C([O-])(O)=O.[Na+]>C1COCC1>[CH3:17][C:8]1[N:9]=[CH:10][C:11]2[C:16]([C:7]=1[CH:21]=[O:22])=[CH:15][CH:14]=[CH:13][CH:12]=2

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 37777034-Bromo-3-methyl-isoquinolineHCID 178418339Butyllithium

Product 1

HCID 234992053-Methylisoquinoline-4-carbaldehydeYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of n-BuLi (2.5M, 0.869 ml, 2.17 mmol)) in 10 ml anhydrous THF at −50° C., 4-bromo-3-methylisoquinoline (0.460 g, 2.07 mmol) was added. After 10 minutes of stirring, DMF (0.32 g, 4.14 mmol) was added to the solution. The reaction mixture was allowed to stir at −50° C. for 20 minutes and then at room temperature for 15 minutes. 5 ml of 1N HCl was added and the solution was stirred for another 5 minutes. The reaction mixture was neutralized with saturated solution of NaHCO3 (25 ml) and partitioned between ethylacetate (2×20 ml) and water (10 ml). The organic layer was dried over sodium sulfate, filtered, concentrated and column purified (hexane:EtOAc; 3:2) to give 0.151 g (43%) of the product as a syrup.

Workup

  1. stirringto stir at −50° C. for 20 minutes
  2. waitat room temperature for 15 minutes
  3. stirringthe solution was stirred for another 5 minutes
  4. custompartitioned between ethylacetate (2×20 ml) and water (10 ml)
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customcolumn purified (hexane:EtOAc; 3:2)

Sources & evidence

ORD record
ord-8a6e5117bbb04f779dceac16f7e7602f
Source dataset
uspto-grants-2001_09
Patent number
US06294566B1

Reaction notes

Loading…