Réaction #63517

Équation de réaction

N-(4-aminophenethyl)-1,2,3,4-tetrahydro-6-methoxy-1-methylisoquinoline

formic acid

→

N-(4-formamidophenethyl)-1,2,3,4-tetrahydro-6 -methoxy-1-methylisoquinoline

Solvants

toluene

Conditions de réaction

Traitement

1. 1
   Températureto reflux
2. 2
   Autrewater was collected by a Dean-Stark apparatus
3. 3
   workup.ADDITIONthe reaction was poured into ice water (500 g)
4. 4
   AutreThe toluene layer was separated
5. 5
   Extractionthe aqueous layer was extracted further with toluene (1×200 ml)
6. 6
   Autredried
7. 7
   Concentrationconcentrated to an oil
8. 8
   workup.DISSOLUTIONThe oil was dissolved in 100 ml ether
9. 9
   Autrea solid formed which
10. 10
    Filtrationwas filtered off
11. 11
    Autredried

Mode opératoire

To a stirred solution of N-(4-aminophenethyl)-1,2,3,4-tetrahydro-6-methoxy-1-methylisoquinoline (16.8 g, 0.057 m) in 800 ml toluene was added formic acid (25.0 g, 0.5 m). The reaction was brought to reflux, and water was collected by a Dean-Stark apparatus. After 1 hour, the reaction was poured into ice water (500 g) and basified to pH 11-12 with 10% NaOH. The toluene layer was separated, and the aqueous layer was extracted further with toluene (1×200 ml) and then with chloroform (2×200 ml). The organic extracts were combined, dried and concentrated to an oil. The oil was dissolved in 100 ml ether and a solid formed which was filtered off and dried to give N-(4-formamidophenethyl)-1,2,3,4-tetrahydro-6 -methoxy-1-methylisoquinoline, wt. 12.0 g (71%), m.p. 93°-96°.

Source