Water → (+/-) 7-Amino-1,2-dimethyl-tetrahydroisoquinoline

HRID 650949Notes

Reaction equation

[I-].[NH2:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7](Cl)=[C:8](Cl)[N+:9]([CH3:13])=[CH:10]2)=[CH:5][CH:4]=1.[CH3:16][Mg]Cl.O>O1CCCC1>[NH2:2][C:3]1[CH:12]=[C:11]2[CH:6]([CH2:7][CH2:8][N:9]([CH3:13])[CH:10]2[CH3:16])[CH2:5][CH:4]=1

Participants

Conditions

Temperature: -78 °C

Procedure

(±) 7-Amino-2-methyl-3,4-dichloroisoquinolinium iodide (0.50 g, 1.7 mmol) was suspended in anhydrous tetrahydrofuran (50 ml) and cooled to −78° C. The cooled solution was treated with methyl magnesium chloride (2.14 ml of a 3M solution in THF, 6.96 mmol), added as a single portion. The reaction was allowed to reach room temperature over 18 h before being poured into water (50 ml). The organic solvent was removed in vacuo and the organic product extracted into dichloromethane. Drying over magnesium sulfate and evaporation in vacuo fuinished the title compound as a pale yellow oil (0.3 g, 98%). For ease of handling the product was converted into a monohydrochloride.

Workup

additionadded as a single portion
customThe organic solvent was removed in vacuo
extractionthe organic product extracted into dichloromethane
dry with materialDrying over magnesium sulfate and evaporation in vacuo

Sources & evidence

ORD record: ord-48d8844025244411a3f29f041176d44e
Source dataset: uspto-grants-2001_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06277861B1

Reaction notes

Loading…