Dimethylformamide → 3H-Naphtho[1,2,3-de]quinoline-1-carbonitrile, 2,7-dihydro-6-[[4-(2-hydroxyethyl)phenyl]amino]-3-methyl-2,7-dioxo-

HRID 1656089

반응식

HRID 1656089 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH3:23])[C:7](=[O:22])[C:8]([C:20]#[N:21])=[C:9]3[C:14]=2[C:13]=1[C:12](=[O:15])[C:11]1[CH:16]=[CH:17][CH:18]=[CH:19][C:10]3=1.N[C:25]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)(O)C.[C:34](=[O:37])([O-])[O-].[K+].[K+].C[N:41](C)C=O>C(O)(C)C>[C:20]([C:8]1[C:7](=[O:22])[N:6]([CH3:23])[C:5]2[CH:4]=[CH:3][C:2]([NH:41][C:31]3[CH:32]=[CH:33][C:28]([CH2:25][CH2:34][OH:37])=[CH:29][CH:30]=3)=[C:13]3[C:12](=[O:15])[C:11]4[CH:16]=[CH:17][CH:18]=[CH:19][C:10]=4[C:9]=1[C:14]=23)#[N:21]

참가 물질

6

반응물 4

HCID 6228Dimethylformamide2회HCID 11430Potassium CarbonateHCID 111220753H-Naphtho[1,2,3-de]quinoline-1-carbonitrile, 6-bromo-2,7-dihydro-3-methyl-2,7-dioxo-HCID 13388400Aminophenylethanol

생성물 1

HCID 1639963H-Naphtho[1,2,3-de]quinoline-1-carbonitrile, 2,7-dihydro-6-[[4-(2-hydroxyethyl)phenyl]amino]-3-methyl-2,7-dioxo-수율 8.13%

시약·촉매·용매 1

HCID 3776Isopropanol용매

반응 조건

온도
70 °C

실험 절차

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 8.13% of 1-cyano-6-[4-(2-hydroxyethyl)anilino]-3-methyl-3-H 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-bromo anthraquinone, Was 0.97×0.844×0.813×100 or 66.6%

후처리

  1. additionwere mixed
  2. temperatureThe temperature was then increased to about 80° C.
  3. temperatureincreased to about 90° C.
  4. waitheld for 1 hr
  5. temperatureincreased to about 100° C.
  6. waitheld for 1 hr
  7. temperaturefinally increased to 110° C.
  8. waitheld for 2 hrs
  9. temperatureto cool to room temperature
  10. filtrationThe product was collected by filtration
  11. washwashed with isopropanol, water and again with isopropanol
  12. customAfter drying the product
  13. custom34.97 g (85.5% weight yield)

출처 및 근거

ORD 기록
ord-d714051bc61541f9bff15a1886f9657d
출처 데이터셋
uspto-grants-1993_10
특허 번호
US05252699

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