Ammonium Chloride → 6-Amino-4-[(3-bromo-4-fluorophenyl)amino]-7-methoxy-3-quinolinecarbonitrile

HRID 612134Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 612134
[Br:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:23][CH3:24])=[C:17]([N+:20]([O-])=O)[CH:18]=3)[N:13]=[CH:12][C:11]=2[C:25]#[N:26])[CH:5]=[CH:6][C:7]=1[F:8].[Cl-].[NH4+]>O.CO.C(OCC)(=O)C.[Fe]>[NH2:20][C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][C:16]=1[O:23][CH3:24])[N:13]=[CH:12][C:11]([C:25]#[N:26])=[C:10]2[NH:9][C:4]1[CH:5]=[CH:6][C:7]([F:8])=[C:2]([Br:1])[CH:3]=1

Komponenten

7

Edukt 2

HCID 25517Ammonium ChlorideHCID 224666584-[(3-Bromo-4-fluorophenyl)amino]7-methoxy-6-nitro-quinoline-3-carbonitrile

Produkt 1

HCID 224666136-Amino-4-[(3-bromo-4-fluorophenyl)amino]-7-methoxy-3-quinolinecarbonitrileAusbeute 78,4 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 23925IronKatalysatorHCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 2.9 g (6.95 mmol) of 4-[(3-bromo-4-fluorophenyl)amino]7-methoxy-6-nitro-quinoline-3-carbonitrile, 6.5 g (121.6 mmol) of ammonium chloride and 4.05 g (73 mmol) of iron in 50 ml of water and 50 ml of methanol for 6 hours. The mixture was diluted with hot ethyl acetate and the hot mixture was filtered. The filtration was washed with saturated sodium chloride solution then the organic layer was dried over sodium sulfate. The solvent was removed and the residue was chromatographed on silica gel eluting with mixture of ethyl acetate and methanol to give 2.11 g of light yellow solid: mass spectrum (electrospray, m/e): M+H 386.7 and 388.8.

Aufarbeitung

  1. filtrationthe hot mixture was filtered
  2. filtrationThe filtration
  3. washwas washed with saturated sodium chloride solution
  4. dry with materialthe organic layer was dried over sodium sulfate
  5. customThe solvent was removed
  6. customthe residue was chromatographed on silica gel eluting with mixture of ethyl acetate and methanol

Quellen und Nachweise

ORD-Eintrag
ord-66c58c14b1c44930ac7840701fce9e5c
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US06002008

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