تفاعل #61357

معادلة التفاعل

ethyl benzoylacetate

m-anisidine

HCl dioxane

ester c

→

4-hydroxy-2-phenyl-7-methoxyquinoline

المذيبات

toluene

ظروف التفاعل

المعالجة

1. 1
   غسيلThe 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
   تجفيفThe toluene phase was dried (MgSO4)
3. 3
   ترشيحfiltered
4. 4
   تركيزconcentrated under reduced pressure
5. 5
   أخرىto give
6. 6
   workup.DISTILLATIONwhile distilling
7. 7
   أخرىThe cooled dark solid obtained
8. 8
   أخرىwas triturated with CH2Cl2 (200 mL)
9. 9
   ترشيحThe suspension was filtered
10. 10
    غسيلthe resulting solid washed with CH2Cl2
11. 11
    أخرىto give e (22.6 g, 17% from a) as a beige solid

الإجراء التجريبي

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).

المصدر