4-Chloro-2-fluoroaniline → 4-(4-Chloro-2-fluoro-phenylamino)-7-(3-chloro-propoxy)-6-methoxy-quinoline-3-carbonitrile

HRID 612033Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 612033
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10](Cl)=[C:11]([C:16]#[N:17])[CH:12]=[N:13]2)=[CH:8][C:7]=1[O:19][CH3:20].[Cl:21][C:22]1[CH:28]=[CH:27][C:25]([NH2:26])=[C:24]([F:29])[CH:23]=1.Cl.N1C=CC=CC=1.C(=O)(O)[O-].[Na+]>C(OCCO)C>[Cl:21][C:22]1[CH:28]=[CH:27][C:25]([NH:26][C:10]2[C:9]3[C:14](=[CH:15][C:6]([O:5][CH2:4][CH2:3][CH2:2][Cl:1])=[C:7]([O:19][CH3:20])[CH:8]=3)[N:13]=[CH:12][C:11]=2[C:16]#[N:17])=[C:24]([F:29])[CH:23]=1

Komponenten

6

Edukt 4

HCID 938984-Chloro-2-fluoroanilineHCID 516892Sodium BicarbonateHCID 10176127Pyridinium chlorideHCID 112206374-Chloro-7-(3-chloropropoxy)-6-methoxyquinoline-3-carbonitrile

Produkt 1

HCID 102022744-(4-Chloro-2-fluoro-phenylamino)-7-(3-chloro-propoxy)-6-methoxy-quinoline-3-carbonitrileAusbeute 68,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8076Glycol monoethyl etherLösungsmittel

Versuchsvorschrift

A mixture of 3.1 g (9.96 mmol) of 7-(3-Chloro-propoxy)-4-chloro-6-methoxy-quinoline-3-carbonitrile, 1.6 g (10.96 mmol) of 4-chloro-2-fluoro-aniline, and 1.2 g (10 mmol) of pyridine hydrochloride in 31 ml of 2-ethoxyethanol was stirred at reflux for 1.5 hr. The mixture was poured into saturated sodium bicarbonate solution and extracted with ethyl acetate. The organic solution was dried and solvent was removed. The residue was purified on a silica gel column eluting with chloroform-ether mixtures to give 2.88 g of the title compound as an off-white solid powder: mass spectrum (electrospray, m/e) M+H 419.7.

Aufarbeitung

  1. temperatureat reflux for 1.5 hr
  2. extractionextracted with ethyl acetate
  3. customThe organic solution was dried
  4. customsolvent was removed
  5. customThe residue was purified on a silica gel column
  6. washeluting with chloroform-ether mixtures

Quellen und Nachweise

ORD-Eintrag
ord-67b9bfde143d463698e74e117208e398
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US06002008

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