1,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene) → Ethyl 7-hydroxyquinoline-3-carboxylate

HRID 1748370Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1748370
O[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12]C)=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15].C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1.COC1C=C(NC=C(C(OCC)=O)C(OCC)=O)C=CC=1>>[OH:12][C:8]1[CH:7]=[C:6]2[C:11]([CH:2]=[C:3]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:4]=[N:5]2)=[CH:10][CH:9]=1

Komponenten

4

Edukt 3

HCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)HCID 3904966Diethyl 2-(((3-methoxyphenyl)amino)methylene)malonateHCID 178469633HCID 178469633, Verbindung

Produkt 1

HCID 135819170Ethyl 7-hydroxyquinoline-3-carboxylateAusbeute 90 %

Versuchsvorschrift

Ethyl 4-hydroxy-7-methoxyquinoline-3-carboxylate. To a solution of boiling Dowtherm™ (100 mL) was added diethyl 2-(((3-methoxyphenyl)amino)methylene)malonate (20.0 g, 68.3 mmol). After 15 minutes the reaction was cooled to ambient temperature and poured into hexanes (500 mL). The precipitate was collected by filtration and dried under high vacuum to yield the title compound as a brown solid (15.2 g, 90%). 1H NMR (400 MHz, DMSO-d6) δ 12.09 (d, J=5.9 Hz, 1H), 8.47 (d, J=6.7 Hz, 1H), 8.03 (d, J=9.4 Hz, 1H), 7.04-6.97 (m, 2H), 4.18 (q, J=7.0 Hz, 2H), 3.85 (s, 3H), 1.25 (t, J=7.2 Hz, 4H).

Aufarbeitung

  1. filtrationThe precipitate was collected by filtration
  2. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-459b2d28601b455a9965065114d42db6
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09150572B2

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