Water → 6-amino-8-fluoro-1-methyl-3,4-dihydro-1H-quinolin-2-one

HRID 723913Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 723913
[F:1][C:2]1[CH:3]=[C:4]([N+:14]([O-])=O)[CH:5]=[C:6]2[C:11]=1[N:10]([CH3:12])[C:9](=[O:13])[CH2:8][CH2:7]2.O.[Cl-].[NH4+].ClCCl>C(O)C.[Fe]>[NH2:14][C:4]1[CH:5]=[C:6]2[C:11](=[C:2]([F:1])[CH:3]=1)[N:10]([CH3:12])[C:9](=[O:13])[CH2:8][CH2:7]2

Komponenten

7

Edukt 4

HCID 962WaterHCID 6344DichloromethaneHCID 25517Ammonium ChlorideHCID 218779148-fluoro-1-methyl-6-nitro-3,4-dihydro-1H-quinolin-2-one

Produkt 1

HCID 218777156-amino-8-fluoro-1-methyl-3,4-dihydro-1H-quinolin-2-oneAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

8-Fluoro-1-methyl-6-nitro-3,4-dihydro-1H-quinolin-2-one (Step 2, 2.28 g, 0.0102 mol) is heated in ethanol (75 ml) until dissolved. Water (25 ml) and ammonium chloride (5.46 g, 0.102 mol) are added and the mixture heated to 90° C. Iron powder (2.27 g, 0.0407 mol) is added portionwise and the mixture stirred and heated for 30 minutes. The reaction is cooled and dichloromethane (200 ml) added. The mixture is filtered and the organic layer separated, washed with saline, dried (MgSO4) and evaporated to give the title compound as a yellow solid (1.98 g, 99%); [M+H]+=195.

Aufarbeitung

  1. dissolutionuntil dissolved
  2. temperatureheated for 30 minutes
  3. temperatureThe reaction is cooled
  4. filtrationThe mixture is filtered
  5. customthe organic layer separated
  6. washwashed with saline
  7. dry with materialdried (MgSO4)
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-2ec04062e1824e9d9f9fdea53fbf6518
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07141588B2

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