反応 #1829904

反応方程式

potassium carbonate

N,N-dimethylformamide

N,N-dimethylformamide

6-bromo-1-cyano-3-methyl-3H-dibenz[f,ij]isoquinoline-2,7-dione

p-aminophenylethanol

→

1-cyano-6-[4-(2-hydroxyethyl)anilino]-3-methyl-3H-dibenz[f,ij]isoquinoline-2,7-dione

収率 81.3%

溶媒

isopropanol

反応条件

後処理

1. 1
   workup.ADDITIONwere mixed
2. 2
   温度The temperature was then increased to about 80° C.
3. 3
   温度increased to about 90° C.
4. 4
   workup.WAITheld for 1 hr
5. 5
   温度increased to about 100° C.
6. 6
   workup.WAITheld for 1 hr
7. 7
   温度finally increased to 110° C.
8. 8
   workup.WAITheld for 2 hrs
9. 9
   温度to cool to room temperature
10. 10
    ろ過The product was collected by filtration
11. 11
    洗浄washed with isopropanol, water and again with isopropanol
12. 12
    その他After drying the product
13. 13
    その他34.97 g (85.5% weight yield)

実験手順

A sample of 6-bromo-1-cyano-3-methyl-3H-dibenz[f,ij]isoquinoline-2,7-dione (36.5 g of 96% assay material - 35.0 g pure material, 0.10 m) prepared is in Example 2, p-aminophenylethanol (55.0 g), potassium carbonate (10.0 g), cupric acetate (12.0 g) and N,N-dimethylformamide (100 ml) were mixed and heated at about 70° C. for 1 hr. The temperature was then increased to about 80° C. and held for 1 hr, increased to about 90° C. and held for 1 hr, increased to about 100° C. and held for 1 hr and finally increased to 110° C. and held for 2 hrs. Additional N,N-dimethylformamide (140 ml) and isopropanol (280 ml) were added at about 80° C. and the reaction mixture allowed to cool to room temperature. The product was collected by filtration, washed with isopropanol, water and again with isopropanol. After drying the product weighed 34.97 g (85.5% weight yield) and was determined to have an assay of 95.2% by high pressure liquid chromatography to give an assay yield of 0.952×0.855×100 or 81.3% of 1-cyano-6-[4-(2-hydroxyethyl)anilino]-3-methyl-3H-dibenz[f,ij]isoquinoline-2,7-dione. The product as produced was very pure and did not require further purification by recrystallization. The overall percent assay yield for the three steps, based on starting with 1-methylamino-4-bromoanthraquinone, was 0.97×0.844×0.813×100 or 66.6%.

出典