Реакция #9453

Уравнение реакции

7-bromo—N4-isobutylquinoline-3,4-diamine

ethoxyacetyl chloride

→

7-bromo-2-ethoxymethyl-1-isobutyl-1H-imidazo[4,5-c]quinoline

Выход 41.1%

Растворители

pyridine

Условия реакции

Обработка

1. 1
   Температураwas then heated in an oil bath
2. 2
   КонцентрированиеThe reaction mixture was concentrated under vacuum
3. 3
   Промывкаwashed with 2M Na2CO3 (2×)
4. 4
   СушкаThe organic layer was dried (MgSO4)
5. 5
   Фильтрацияfiltered
6. 6
   Концентрированиеconcentrated
7. 7
   ДругоеRecrystallization of the resulting solid

Методика

A solution of 7-bromo—N4-isobutylquinoline-3,4-diamine (85 g, prepared according to Part F of Example 1) in anhydrous pyridine (413 mL) was immersed in an ice bath, and ethoxyacetyl chloride (36.9 g, 300 mmol) was added. The reaction was allowed to warm to room temperature and was then heated in an oil bath held at 85° C. for 3.5 h. The reaction mixture was concentrated under vacuum, and the residue was taken up in diethyl ether and washed with 2M Na2CO3 (2×) followed by H2O (1×). The organic layer was dried (MgSO4), filtered, and concentrated. Recrystallization of the resulting solid from boiling 15% ethyl acetate in hexanes afforded 43.0 g of 7-bromo-2-ethoxymethyl-1-isobutyl-1H-imidazo[4,5-c]quinoline as brown crystals.

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