HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → 1-Methoxy-5-methylisoquinolin-4-carbaldehyde
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | HCID 24766191 | HCID 24766191 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 1-Methoxy-5-methylisoquinolin-4-carbaldehyde | HCID 24766193 | 78% |
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
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09006442B2 |
| Source dataset | uspto-grants-2015_04 |
| ORD ID | ord-3dd3eb3795a14a37b236694b78ee47a0 |
| Source note | uspto-grants-2015_04 |