Methanol → 6-Amino-4-(3-chloro-4-fluoroanilino)-3-cyano-7-ethyloxyquinoline

HRID 1935186

Reaktionsgleichung

Reaktionsgleichung von HRID 1935186
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([NH:10][C:11]2[C:20]3[C:15](=[CH:16][C:17]([O:24][CH2:25][CH3:26])=[C:18]([N+:21]([O-])=O)[CH:19]=3)[N:14]=[CH:13][C:12]=2[C:27]#[N:28])[CH:6]=[CH:7][C:8]=1[F:9].[Cl-].[NH4+].CO>O.[Fe]>[NH2:21][C:18]1[CH:19]=[C:20]2[C:15](=[CH:16][C:17]=1[O:24][CH2:25][CH3:26])[N:14]=[CH:13][C:12]([C:27]#[N:28])=[C:11]2[NH:10][C:5]1[CH:6]=[CH:7][C:8]([F:9])=[C:3]([Cl:2])[CH:4]=1

Komponenten

6

Edukt 3

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 224665794-((3-Chloro-4-fluorophenyl)amino)-7-ethoxy-6-nitroquinoline-3-carbonitrile hydrochloride

Produkt 1

HCID 110356856-Amino-4-(3-chloro-4-fluoroanilino)-3-cyano-7-ethyloxyquinoline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

4-(3-Chloro-4-fluoro-phenylamino)-7-ethoxy-6-nitro-quinoline-3-carbonitrile hydrochloride (38.6 g 91.2 mmol) was mixed with 35.7 g (638 mmol) of iron powder. A solution of 43.9 g (820 mmol) of ammonium chloride in 280 ml of water was added followed by 985 ml of methanol. The mixture was reflux with mechanical stirring under nitrogen for 4 hr at which time TLC indicated complete reduction. The reaction mixture was filtered hot and solids were washed with 500 ml of boiling methanol. After the combined filtrate was evaporated, the residue was partitioned between 1.5L of warm ethyl acetate and 700 ml of saturated sodium bicarbonate solution. The organic layer was dried over magnesium sulfate, treated with Norite, filtered and evaporated to give a solid which was recrystallized from CHCl3-hexanes giving 29.0 g (89%) of 6-amino-4-(3-chloro-4-fluoro-phenylamino)-7-ethoxy-quinoline-3-carbonitrile as a light green solid.

Aufarbeitung

  1. temperatureThe mixture was reflux
  2. filtrationThe reaction mixture was filtered hot
  3. washsolids were washed with 500 ml of boiling methanol
  4. customAfter the combined filtrate was evaporated
  5. customthe residue was partitioned between 1.5L of warm ethyl acetate and 700 ml of saturated sodium bicarbonate solution
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. additiontreated with Norite
  8. filtrationfiltered
  9. customevaporated
  10. customto give a solid which
  11. customwas recrystallized from CHCl3-hexanes giving 29.0 g (89%) of 6-amino-4-(3-chloro-4-fluoro-phenylamino)-7-ethoxy-quinoline-3-carbonitrile as a light green solid

Quellen und Nachweise

ORD-Eintrag
ord-b1e8a7058d5246a3bd22db9d1866d7c9
Quelldatensatz
uspto-grants-2002_05
Patentnummer
US06384051B1

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