Dimethylformamide → 1-Methoxy-5-methylisoquinolin-4-carbaldehyde

HRID 1470458Notes

Reaction equation

HRID 1470458 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[CH3:12])[C:5]([O:13][CH3:14])=[N:4][CH:3]=1.[Li]CCCC.CN([CH:23]=[O:24])C>C1COCC1>[CH3:14][O:13][C:5]1[C:6]2[C:11](=[C:10]([CH3:12])[CH:9]=[CH:8][CH:7]=2)[C:2]([CH:23]=[O:24])=[CH:3][N:4]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24766191HCID 24766191, compoundHCID 178418339Butyllithium

Product 1

HCID 247661931-Methoxy-5-methylisoquinolin-4-carbaldehydeYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of 4-bromo-1-methoxy-5-methylisoquinoline (Intermediate-6) (2 g, 7.9 mmol) in dry THF (20 mL) was added, n-BuLi (15 mL, 23.7 mmol) drop wise at −78° C. under N2 atmosphere and stirred for 1 h. To this, dry DMF (3 mL) was added and the reaction mixture was stirred at −78° C. for another 1 h. Then it was quenched with saturated NH4Cl solution, extracted with EtOAc (3×100 mL), washed with water (1×200 mL), dried over Na2SO4, filtered and concentrated to afford the title compound (1.2 g, 78%).

Workup

  1. customThen it was quenched with saturated NH4Cl solution
  2. extractionextracted with EtOAc (3×100 mL)
  3. washwashed with water (1×200 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3dd3eb3795a14a37b236694b78ee47a0
Source dataset
uspto-grants-2015_04
Patent number
US09006442B2

Reaction notes

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