2-Cyano-3-[5-(methylsulfanyl)-2-nitrophenyl]prop-2-enamide → 6-Methylthio-2-Aminoquinoline-3-Carboxamide

HRID 1112258

Reaktionsgleichung

Reaktionsgleichung von HRID 1112258
[C:1]([C:3](=[CH:7][C:8]1[CH:13]=[C:12]([S:14][CH3:15])[CH:11]=[CH:10][C:9]=1[N+:16]([O-])=O)[C:4]([NH2:6])=[O:5])#[N:2]>C(O)(=O)C.CN(C)C=O.[Fe]>[CH3:15][S:14][C:12]1[CH:13]=[C:8]2[C:9](=[CH:10][CH:11]=1)[N:16]=[C:1]([NH2:2])[C:3]([C:4]([NH2:6])=[O:5])=[CH:7]2

Komponenten

4

Edukt 1

HCID 539198542-Cyano-3-[5-(methylsulfanyl)-2-nitrophenyl]prop-2-enamide

Produkt 1

HCID 227528206-Methylthio-2-Aminoquinoline-3-Carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysator2×HCID 21926011acetic acid N,N-dimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

A mixture of α-cyano-β-(2-nitro-5-methylthiophenyl)acrylamide (8.4 g., 0.032 mole) in acetic acid - N,N-dimethylformamide (110 ml. of 1:1) is heated in a 75° C. bath. Iron powder (2.0g.) is added and the mixture stirred until the internal temperature rose to 95° C. Additional iron powder (6.16 g. total iron added = 0.146 mole) is added in small portions over a 15-minute period. The reaction mixture is stirred for 1 hour following completion of addition and then filtered hot. The iron residue is washed with hot acetic acid and the combined filtrate and wash solution poured into IN hydrochloric acid (200 ml.). The hydrochloride salt which separates is filtered off and dissolved in hot dilute aqueous sodium hydroxide. The yellow solid which separates on cooling is filtered off, washed with isopropyl alcohol and air-dried. Yield = 3.26 g. (44%); M.P. 229°-242° C.

Aufarbeitung

  1. customrose to 95° C
  2. stirringThe reaction mixture is stirred for 1 hour
  3. additioncompletion of addition
  4. filtrationfiltered hot
  5. washThe iron residue is washed with hot acetic acid
  6. washthe combined filtrate and wash solution
  7. additionpoured into IN hydrochloric acid (200 ml.)
  8. filtrationThe hydrochloride salt which separates is filtered off
  9. dissolutiondissolved in hot dilute aqueous sodium hydroxide
  10. temperatureon cooling
  11. filtrationis filtered off
  12. washwashed with isopropyl alcohol
  13. customair-dried

Quellen und Nachweise

ORD-Eintrag
ord-c48016a2d8b9429e80cc4aebd0937ba3
Quelldatensatz
uspto-grants-1978_10
Patentnummer
US04120962

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