5-Amino-2-methylphenol → 7-Ethoxy-4-[(3-hydroxy-4-methylphenyl)amino]-6-methoxy-3-quinolinecarbonitrile

HRID 612113

Reaktionsgleichung

Reaktionsgleichung von HRID 612113
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH3:16])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:17]#[N:18].[OH:19][C:20]1[CH:21]=[C:22]([CH:24]=[CH:25][C:26]=1[CH3:27])[NH2:23]>C(O)C>[CH2:15]([O:14][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([NH:23][C:22]3[CH:24]=[CH:25][C:26]([CH3:27])=[C:20]([OH:19])[CH:21]=3)=[C:3]([C:17]#[N:18])[CH:4]=[N:5]2)=[CH:10][C:9]=1[O:12][CH3:13])[CH3:16]

Komponenten

4

Edukt 2

HCID 178185-Amino-2-methylphenolHCID 105634734-Chloro-7-ethoxy-6-methoxy-3-quinolinecarbonitrile

Produkt 1

HCID 224667527-Ethoxy-4-[(3-hydroxy-4-methylphenyl)amino]-6-methoxy-3-quinolinecarbonitrileAusbeute 54,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 500 mg (1.90 mmol) 4chloro-7ethoxy-6-methoxy-3-quinolinecarbonitrile, 30 ml ethanol, and 281 mg (2.28 mmol) 3-hydroxy-4-methylaniline was heated to reflux under N2 overnight. Removed heat and made basic with saturated sodium bicarbonate. Stripped solvents and slurried residue in hexane. Collected solids, washed with water, and dried in vacuo, giving 364 mg off-white solid: mass spectrum (electrospray m/e): M+H=349.9.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux under N2 overnight
  3. customRemoved
  4. temperatureheat
  5. customCollected solids
  6. washwashed with water
  7. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-2257594767904b8c8d0de3e04236adb3
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US06002008

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