反应详情

2-(3-Methoxy-4-pent-2-ynyloxy-benzyloxy)-isoindole-1,3-dione (27 g, 74 mmol) is suspended in a mixture of 500 ml of methanol and 50 ml of N,N-dimethylformamide. After heating this mixture to +60° C., hydrazine hydrate (8.5 g, 0.17 mol) is added. The reaction is stirred for 3 hours at +60° C. and subsequently cooled down to room temperature. A mixture of 28 ml of concentrated hydrochloric acid and 80 ml of water is added to acidify the resulting suspension. Then it is filtered to remove a precipitation and the solid is washed with water/methanol. The filtrate is concentrated in vacuo to one third of its original volume. Sodium hydroxide (18 g, mol in 90 ml water) is added to the remainder and this mixture is extracted with diethyl ether. The combined organic layer is washed with water and brine, dried over magnesium sulfate and evaporated to give O-(3-methoxy-4-pent-2-ynyloxy-benzyl)-hydroxylamine as yellow oil.

1. temperatureAfter heating this mixture to +60° C.
2. additionis added
3. filtrationThen it is filtered
4. customto remove
5. customa precipitation
6. washthe solid is washed with water/methanol
7. concentrationThe filtrate is concentrated in vacuo to one third of its original volume
8. additionSodium hydroxide (18 g, mol in 90 ml water) is added to the remainder
9. extractionthis mixture is extracted with diethyl ether
10. washThe combined organic layer is washed with water and brine
11. dry with materialdried over magnesium sulfate
12. customevaporated