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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1470458Generated: October 31, 2026

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

https://huagongshe.com/reaction/1470458

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantHCID 24766191HCID 24766191—
ReactantButyllithiumHCID 178418339—
SolventTetrahydrofuranHCID 8028—
Product1-Methoxy-5-methylisoquinolin-4-carbaldehydeHCID 2476619378%

Reaction Conditions

Temperature-78 °C

Reaction Steps

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%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09006442B2
Source datasetuspto-grants-2015_04
ORD IDord-3dd3eb3795a14a37b236694b78ee47a0
Source noteuspto-grants-2015_04