alpha-Cyano-beta-(2-Nitro-5-Fluorophenyl)Acrylamide → 6-Fluoro-2-Aminoquinoline-3-Carboxamide

HRID 2163578Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2163578
[C:1]([C:3](=[CH:7][C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=1[N+:15]([O-])=O)[C:4]([NH2:6])=[O:5])#[N:2]>C(O)(=O)C.[Fe]>[F:14][C:12]1[CH:13]=[C:8]2[C:9](=[CH:10][CH:11]=1)[N:15]=[C:1]([NH2:2])[C:3]([C:4]([NH2:6])=[O:5])=[CH:7]2

Komponenten

4

Edukt 1

HCID 53864188alpha-Cyano-beta-(2-Nitro-5-Fluorophenyl)Acrylamide

Produkt 1

HCID 227528386-Fluoro-2-Aminoquinoline-3-Carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysator2×HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

Iron powder (8.52 g., 0.152 mole) is gradually added over a forty minute period to a slurry of α-cyano-β-(2-nitro-5-fluorophenyl)acrylamide (7.97 g., 0.034 mole) in acetic acid (100 ml.) at 85° C. When addition of the iron powder is complete, the mixture is heated to 95°-100° C. for 1.5 hours and then filtered hot through diatomaceous earth. The filtrate is cooled in an ice bath and then filtered to give a tan crystalline solid. The solid is partitioned between ethyl acetate and water, the organic phase separated, dried over anhydrous sodium sulfate and concentrated to yield 6.34 g. (90%) of the title amide as yellow crystals. M.P. 232°-236° C.

Aufarbeitung

  1. temperaturethe mixture is heated to 95°-100° C. for 1.5 hours
  2. filtrationfiltered hot through diatomaceous earth
  3. temperatureThe filtrate is cooled in an ice bath
  4. filtrationfiltered
  5. customto give a tan crystalline solid
  6. customThe solid is partitioned between ethyl acetate and water
  7. customthe organic phase separated
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated
  10. customto yield 6.34 g

Quellen und Nachweise

ORD-Eintrag
ord-c2aabc0ae453433fa77b68bc08943800
Quelldatensatz
uspto-grants-1979_01
Patentnummer
US04134981

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