1,2-Dimethoxyethane → 4-(4-Cyanoquinoline-2-yl)-2-hydroxy-benzoic acid methyl ester

HRID 2383346Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2383346
Cl[C:2]1[CH:11]=[C:10]([C:12]#[N:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:14][O:15][C:16](=[O:36])[C:17]1[CH:22]=[CH:21][C:20](B2OC(C)(C)C(C)(C)O2)=[CH:19][C:18]=1[O:32]COC.C(=O)([O-])[O-].[Na+].[Na+].C(COC)OC>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(OCC)(=O)C.O>[CH3:14][O:15][C:16](=[O:36])[C:17]1[CH:22]=[CH:21][C:20]([C:2]2[CH:11]=[C:10]([C:12]#[N:13])[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=2)=[CH:19][C:18]=1[OH:32]

Komponenten

8

Edukt 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 228320822-Chloroquinoline-4-carbonitrileHCID 673097342-Methoxymethoxy-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolane-2-yl)benzoic acid methyl ester

Produkt 1

HCID 673109994-(4-Cyanoquinoline-2-yl)-2-hydroxy-benzoic acid methyl esterAusbeute 41,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

2-Chloroquinoline-4-carbonitrile (0.15 g), 2-methoxymethoxy-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolane-2-yl)benzoic acid methyl ester (0.26 g), tetrakis(triphenylphosphine)palladium (0.045 g) and sodium carbonate (0.16 g) were suspended in a mixed solvent of dimethoxyethane (2 mL) and water (0.5 mL), and the resulting mixture was stirred at 150° C. for 30 minutes using microwave reactor (Biotage). To the reaction mixture was added ethyl acetate, and the mixture was filtered through a Celite pad. The filtrate was poured into water. The organic layer was washed with water and brine, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=100/0-66/34) to give 4-(4-cyanoquinoline-2-yl)-2-hydroxy-benzoic acid methyl ester (0.1 g). To a mixed solution of this compound (0.1 g) in tetrahydrofuran (4 mL), ethanol (1 mL) and water (1 mL) was added lithium hydroxide monohydrate (0.060 g), and the mixture was stirred at room temperature overnight. To this reaction mixture was added 2 mol/L hydrochloric acid (2.8 mL), and the mixture was stirred at 50° C. for 10 hours. After the reaction mixture was cooled to room temperature, the precipitated solid was collected by filtration, and dried under reduced pressure to give the title compound (0.068 g).

Aufarbeitung

  1. filtrationthe mixture was filtered through a Celite pad
  2. additionThe filtrate was poured into water
  3. washThe organic layer was washed with water and brine
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=100/0-66/34)

Quellen und Nachweise

ORD-Eintrag
ord-55894bf4799447ebab72928d2640f4f5
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08263622B2

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