Реакция #61357

Уравнение реакции

ethyl benzoylacetate

m-anisidine

HCl dioxane

ester c

→

4-hydroxy-2-phenyl-7-methoxyquinoline

Растворители

toluene

Условия реакции

Обработка

1. 1
   ПромывкаThe cooled toluene solution was successively washed with aqueous 10% HCl (2×300 mL), 1 N NaOH (2×300 mL), H2O (300 mL) and brine (150 mL)
2. 2
   СушкаThe toluene phase was dried (MgSO4)
3. 3
   Фильтрацияfiltered
4. 4
   Концентрированиеconcentrated under reduced pressure
5. 5
   Другоеto give
6. 6
   workup.DISTILLATIONwhile distilling
7. 7
   ДругоеThe cooled dark solid obtained
8. 8
   Другоеwas triturated with CH2Cl2 (200 mL)
9. 9
   ФильтрацияThe suspension was filtered
10. 10
    Промывкаthe resulting solid washed with CH2Cl2
11. 11
    Другоеto give e (22.6 g, 17% from a) as a beige solid

Методика

A solution of ethyl benzoylacetate (b) (100.0 g, 0.52 mol), m-anisidine (a) (128.1 g, 1.04 mol) and 4 N HCl/dioxane (5.2 mL) in toluene (1.0 L) was refluxed for 6.25 h in a Dean-Stark apparatus. The cooled toluene solution was successively washed with aqueous 10% HCl (2×300 mL), 1 N NaOH (2×300 mL), H2O (300 mL) and brine (150 mL). The toluene phase was dried (MgSO4), filtered and concentrated under reduced pressure to give a 1.2:1.0 mixture of ester c and amide d (144.6 g, 45%/38% crude yield) as a dark brown oil. The crude oil was heated to 280° C. for 80 min while distilling generated EtOH. The cooled dark solid obtained was triturated with CH2Cl2 (200 mL). The suspension was filtered and the resulting solid washed with CH2Cl2 to give e (22.6 g, 17% from a) as a beige solid: 1H NMR (DMSO-d6) δ 8.00 (d, J=9.0 Hz, 1H), 7.81-7.82 (m, 2H), 7.57-7.59 (m, 3H), 7.20 (d, J=2.2 Hz, 1H), 6.94 (dd, J=9.0, 2.2 Hz, 1H), 6.26 (s, 1H), 3.87 (s, 3H).

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