HCID 66650497, Verbindung → Amino-5-ethoxy-4-trifluoromethyl-benzonitrile

HRID 418145Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 418145
[CH2:1]([O:3][C:4]1[C:5]([C:15]([F:18])([F:17])[F:16])=[CH:6][C:7]([N+:12]([O-])=O)=[C:8]([CH:11]=1)[C:9]#[N:10])[CH3:2]>CO.Cl.[Fe]>[NH2:12][C:7]1[CH:6]=[C:5]([C:15]([F:17])([F:18])[F:16])[C:4]([O:3][CH2:1][CH3:2])=[CH:11][C:8]=1[C:9]#[N:10]

Komponenten

5

Edukt 1

HCID 66650497HCID 66650497, Verbindung

Produkt 1

HCID 66650419Amino-5-ethoxy-4-trifluoromethyl-benzonitrileAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23925IronKatalysatorHCID 313Hydrochloric AcidLösungsmittelHCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Iron powder (40.96 g, 733 mmol) was added in small portions over 5 min to a stirred suspension of finely grinded 5-ethoxy-2-nitro-4-trifluoromethyl-benzonitrile from step 3 (42.79 g, 164.5 mmol) in MeOH (85 mL) and conc. HCl (102 mL) with water bath cooling keeping the internal temperature at 40-50° C. The resulting mixture was stirred for further 1 h at ca. 50° C. and then poured into ice cold H2O (700 mL). The precipitate was filtered, washed with water, dried, and dissolved in boiling EtOH (800 mL), activated carbon (ca. 10 g) was added, the mixture was refluxed for 45 min, the hot solution was filtered and evaporated to dryness to leave a yellow solid (31.81 g, 84%), which was used without further purification. MS (EI) 230.1 [M].

Aufarbeitung

  1. temperaturecooling
  2. customat 40-50° C
  3. filtrationThe precipitate was filtered
  4. washwashed with water
  5. customdried
  6. dissolutiondissolved
  7. additionwas added
  8. temperaturethe mixture was refluxed for 45 min
  9. filtrationthe hot solution was filtered
  10. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-c270145300d541d69037e2f8bbf0d950
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093263B2

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