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

HRID 2092270Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2092270
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

Komponenten

4

Edukt 2

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

Produkt 1

HCID 673394766-Methyl-5-nitro-N-(3-(trifluoromethyl)phenyl)isoquinolin-l-amineAusbeute 81,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
180 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-b90ac211bd964424b23ca6ba2d11ccc9
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08440674B2

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