2,4-Diaminoanisole → Methyl 1-((5-methoxypyridin-2-yl)amino)isoquinoline-5-carboxylate

HRID 1051274

Reaktionsgleichung

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

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

Methyl 1-chloroisoquinoline-5-carboxylate (0.5 g, 2.26 mmol) obtained in Step (1) above was dissolved in 2-propanol (5 mL), and added with 5-amino-p-methoxyaniline (0.33 g, 2.74 mmol) at room temperature. The reaction solution was sealed and stirred for 4 hours or more at 90° C. The reaction mixture was cooled to room temperature, and the solvent was distilled under reduced pressure. The concentrated solid was added with diethyl ether, the solid thus obtained was filtered under reduced pressure. The resulting solid was dried with warm wind in an oven (40° C.) for 3 hours or more to obtain the title compound (0.42 g, 61%).

Aufarbeitung

customThe reaction solution was sealed
temperatureThe reaction mixture was cooled to room temperature
distillationthe solvent was distilled under reduced pressure
additionThe concentrated solid was added with diethyl ether
customthe solid thus obtained
filtrationwas filtered under reduced pressure
customThe resulting solid was dried
temperaturewith warm wind in an oven (40° C.) for 3 hours or more

Quellen und Nachweise

ORD-Eintrag: ord-7c238f88d77f4455b4cbf752ed320990
Quelldatensatz: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09388165B2

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