Phosphorus oxychloride → 7-(3-Chloropropoxy)-4-(2,4-dichloro-5-methoxyanilino)-6-methoxyquinoline-3-carbonitrile

HRID 1593777Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1593777
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:27]=[CH:28][C:29]=1[O:30][CH3:31])[NH:9][CH:10]=[C:11]([C:25]#[N:26])[C:12]([NH:14][C:15]1[CH:20]=[C:19]([O:21][CH3:22])[C:18]([Cl:23])=[CH:17][C:16]=1[Cl:24])=O.P(Cl)(Cl)(Cl)=O>C(#N)C>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:27]([C:12]([NH:14][C:15]3[CH:20]=[C:19]([O:21][CH3:22])[C:18]([Cl:23])=[CH:17][C:16]=3[Cl:24])=[C:11]([C:25]#[N:26])[CH:10]=[N:9]2)=[CH:28][C:29]=1[O:30][CH3:31]

Komponenten

4

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 693108673-(3-chloropropoxy)-4-methoxyanilino-N-(2,4-dichloro-5-methoxyphenyl)-2-cyano-2-propenamide

Produkt 1

HCID 110489207-(3-Chloropropoxy)-4-(2,4-dichloro-5-methoxyanilino)-6-methoxyquinoline-3-carbonitrileAusbeute 45,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A suspension of 3-(3-chloropropoxy)-4-methoxyanilino-N-(2,4-dichloro-5-methoxyphenyl)-2-cyano-2-propenamide (462 mg, 0.95 mmol) in 40 mL of acetonitrile was heated to reflux and phosphorous oxychloride (0.60 mL) was added dropwise, via syringe. The reaction mixture was heated at reflux overnight, then cooled to room temperature and concentrated in vacuo. The residue was cooled to 0° C. and saturated aqueous sodium bicarbonate was added. The mixture was stirred for 10 minutes and the solid was collected by filtration, washed with water. The solid was suspended in hot ethyl acetate and methanol and then filtered to provide 200 mg of 7-(3-chloropropoxy)-4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-methoxy-3-quinolinecarbonitrile as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 2.30 (m, 2H), 3.84 (t, J=6 Hz, 1H), 3.88 (s, 3H), 4.01 (s, 3H), 4.32 (t, J=6 Hz, 2H), 7.46 (s, 1H), 7.51 (s, 1H), 7.81 (s, 1H), 8.14 (s, 1H), 8.81 (s, 1H), 10.83 (br s, 1H), MS (ES) m/z 466.1, 468.1 (M+H)+.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux
  3. temperatureThe reaction mixture was heated
  4. temperatureat reflux overnight
  5. concentrationconcentrated in vacuo
  6. temperatureThe residue was cooled to 0° C.
  7. additionsaturated aqueous sodium bicarbonate was added
  8. filtrationthe solid was collected by filtration
  9. washwashed with water
  10. filtrationmethanol and then filtered

Quellen und Nachweise

ORD-Eintrag
ord-a459a6f5b40d4b62a7b34307efae1ca1
Quelldatensatz
uspto-grants-2007_11
Patentnummer
US07297795B2

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