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

HRID 2092270ノート

反応式

HRID 2092270 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

反応条件

温度
180 °C

実験手順

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 sataturated 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.

後処理

  1. customThe tube was capped
  2. customThe volatiles were removed in vacuo
  3. washwashed with sataturated 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

出典と根拠

ORDレコード
ord-b90ac211bd964424b23ca6ba2d11ccc9
出典データセット
uspto-grants-2013_05
特許番号
US08440674B2

反応ノート

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