3-(Trifluoromethyl)aniline → 6-Methyl-5-nitro-N-(3-(trifluoromethyl)phenyl)isoquinolin-l-amine

HRID 1668912노트

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HRID 1668912 반응식
Cl[C:2]1[C:11]2[C:6](=[C:7]([N+:13]([O-:15])=[O:14])[C:8]([CH3:12])=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[F:16][C:17]([F:26])([F:25])[C:18]1[CH:19]=[C:20]([NH2:24])[CH:21]=[CH:22][CH:23]=1>C(O)(C)C>[CH3:12][C:8]1[C:7]([N+:13]([O-:15])=[O:14])=[C:6]2[C:11](=[CH:10][CH:9]=1)[C:2]([NH:24][C:20]1[CH:21]=[CH:22][CH:23]=[C:18]([C:17]([F:16])([F:25])[F:26])[CH:19]=1)=[N:3][CH:4]=[CH:5]2

참가 물질

4

반응물 2

HCID 73753-(Trifluoromethyl)anilineHCID 226222211-Chloro-6-methyl-5-nitroisoquinoline

생성물 1

HCID 673394766-Methyl-5-nitro-N-(3-(trifluoromethyl)phenyl)isoquinolin-l-amine수율 81.1%

시약·촉매·용매 1

HCID 3776Isopropanol용매

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온도
180 °C

실험 절차

1-Chloro-6-methyl-5-nitroisoquinoline (0.25 g, 1.1 mmol) and 3-(trifluoromethyl)benzenamine (0.17 mL, 1.3 mmol) were added to a microwave tube containing 3 mL of isopropanol. The tube was capped and heated at 180° C. for 1500 seconds. The volatiles were removed in vacuo. The residue was taken up in DCM and washed with saturated NaHCO3. The organic layer was dried with sodium sulfate and purified by column chromatography on silica gel using a gradient of 10 to 40% of ethyl acetate in hexanes to give the product as an orange solid (0.31 g, 79%). MS (M+H)+ 348.

후처리

  1. customThe tube was capped
  2. customThe volatiles were removed in vacuo
  3. washwashed with saturated NaHCO3
  4. dry with materialThe organic layer was dried with sodium sulfate
  5. custompurified by column chromatography on silica gel using a gradient of 10 to 40% of ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-de34fa00b71f4e169f579d51e8639b72
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07989461B2

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