Dimethylformamide → 3,4-Dihydro-1-isopropylisoquinoline-7-carbaldehyde

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

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.