Sulfuric Acid → Ethanol, 2-((4-amino-3-methylphenyl)ethylamino)-, sulfate (1:1)

HRID 2259983

Reaktionsgleichung

Reaktionsgleichung von HRID 2259983
[CH2:1]([N:3]([CH2:11][CH2:12][OH:13])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[CH:5]=1)[CH3:2].[S:14](=[O:18])(=[O:17])([OH:16])[OH:15].[N:19](OC(C)C)=O.[H][H]>[C].[Pd].C(O)(C)C>[S:14]([OH:18])([OH:17])(=[O:16])=[O:15].[NH2:19][C:7]1[CH:8]=[CH:9][C:4]([N:3]([CH2:1][CH3:2])[CH2:11][CH2:12][OH:13])=[CH:5][C:6]=1[CH3:10]

Komponenten

7

Edukt 4

HCID 1118Sulfuric Acid2×HCID 70672-(N-ethyl-m-toluidino)ethanolHCID 10929Isopropyl nitriteHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 91579Ethanol, 2-((4-amino-3-methylphenyl)ethylamino)-, sulfate (1:1)Ausbeute 182,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418390HCID 178418390, VerbindungKatalysatorHCID 3776IsopropanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

With 89.6 g (0.5 mole) of N-ethyl-N-(β-hydroxyethyl)-m-toluidine was mixed 270 ml of 50% v/v isopropanol, and 24.5 g (0.25 mole) of sulfuric acid was added with cooling and stirring at 10° C. or lower. After 49.0 g (0.55 mole) of isopropyl nitrite was added dropwise at 10° C. or lower, the reaction was carried out at 2°-5° C. for another 3 hours. After completion of the reaction, hydrogenation was carried out at 40°-45° C. and at a hydrogen pressure of 3-5 kg/cm2 while adding the nitrosation reaction mixture to 270 ml of 50% v/v isopropanol containing 6.5 g of 5% palladium-carbon over a period of 2 hours. After completion of the hydrogenation, the catalyst was filtered off and the filtrate was concentrated to dryness to remove the solvent. The residue was dissolved in 270 ml of 90% v/v ethanol with heating and 24.5 g (0.25 mole) of sulfuric acid was added at 45°-50° C. Then, the resulting mixture was cooled for 2 hours to carry out crystallization, and the crystals thus formed were collected by filtration at 3° C., washed with 100 ml of cold ethanol, and then dried to obtain 133.3 g of 4-amino-3-methyl-N-ethyl-N-(β-hydroxyethyl)aniline sulfate as white powder. Yield: 91.2%. Melting point: 154.6° C. The purity of 4-amino-3-methyl-N-ethyl-N-(β-hydroxyethyl)aniline sulfate was 100% as measured by HPLC, namely, no impurity was detected at all.

Aufarbeitung

  1. additionwas added
  2. temperaturewith cooling
  3. customAfter completion of the reaction, hydrogenation
  4. additionwhile adding
  5. filtrationAfter completion of the hydrogenation, the catalyst was filtered off
  6. concentrationthe filtrate was concentrated to dryness
  7. customto remove the solvent
  8. dissolutionThe residue was dissolved in 270 ml of 90% v/v ethanol
  9. temperaturewith heating
  10. temperatureThen, the resulting mixture was cooled for 2 hours
  11. customcrystallization
  12. customthe crystals thus formed
  13. filtrationwere collected by filtration at 3° C.
  14. washwashed with 100 ml of cold ethanol
  15. customdried

Quellen und Nachweise

ORD-Eintrag
ord-88ef097be8e842df92b759c9b3a3c901
Quelldatensatz
uspto-grants-1995_12
Patentnummer
US05475140

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