Dimethylformamide → 1-(Propan-2-yl)-3,4-dihydroisoquinoline-7-carbaldehyde

HRID 2298993Notes

Reaction equation

HRID 2298993 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]=[C:9]2[CH:12]([CH3:14])[CH3:13])=[CH:4][CH:3]=1.C([Li])CCC.CN([CH:23]=[O:24])C>C1COCC1>[CH:12]([C:9]1[C:10]2[C:5](=[CH:4][CH:3]=[C:2]([CH:23]=[O:24])[CH:11]=2)[CH2:6][CH2:7][N:8]=1)([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 186800687-Bromo-1-(propan-2-yl)-3,4-dihydroisoquinolineHCID 178418339Butyllithium

Product 1

HCID 117358111-(Propan-2-yl)-3,4-dihydroisoquinoline-7-carbaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of Example 1I (4.7 g, 18.7 mmol) in THF (80 mL) at −78° C. was treated dropwise with 2.5M n-butyllithium in hexanes (9.0 mL, 22.4 mmol), stirred for 20 minutes, treated dropwise with DMF (2.2 mL, 28.0 mmol), stirred for 20 minutes, quenched with saturated NH4Cl, warmed to room temperature, and extracted with diethyl ether. The combined extracts were washed with brine, dried (MgSO4), filtered, and concentrated to provide the desired product.

Workup

  1. stirringstirred for 20 minutes
  2. customquenched with saturated NH4Cl
  3. extractionextracted with diethyl ether
  4. washThe combined extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-553d8b64bee4427dbb881f5e9cbafa3c
Source dataset
uspto-grants-2002_12
Patent number
US06495562B1

Reaction notes

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