Hydrochloric Acid → HCID 20363397, Verbindung

HRID 267500

Reaktionsgleichung

Reaktionsgleichung von HRID 267500
[NH:1]([C:8]1[C:13]([N+:14]([O-])=O)=[CH:12][C:11]([N+:17]([O-])=O)=[C:10]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:27].[H][H]>[Pd].C.CO>[ClH:27].[ClH:27].[NH2:14][C:13]1[C:8]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[N:9][C:10]([NH:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[C:11]([NH2:17])[CH:12]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 21554887HCID 21554887, VerbindungHCID 178418361HCID 178418361, Verbindung2×

Produkt 1

HCID 20363397HCID 20363397, VerbindungAusbeute 181,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14818447PalladiumcarbonKatalysatorHCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

A 500 ml Parr bottle was twice charged with 2,6-dianilino-3,5-dinitropyridine (13.5 g, 0.0385 mole), 300 ml of methanol containing HCl (10 g) and 5% Pd/Charcoal catalyst (1.1 g). The mixture was placed under 55 psig. hydrogen pressure and kept at 25°-40°C until no further uptake of hydrogen was observed. The combined reduction mixtures were cooled, precipitated product and catalyst filtered under nitrogen, and the filter cake washed with 10% HCl in isopropyl alcohol. The filter cake was added to 500 ml of warm (55°C) conc. HCl, stirred well for 5 minutes, filtered and the insolubles washed with conc. HCl. The clear filtrate was cooled (0°C), diluted with 500 ml cold (-15°C) isopropyl alcohol with good stirring to precipitate product. The solid was filtered, washed with 10% HCl in isopropyl alcohol and vacuum dried over P2O5 to afford 3,5-diamino-2,6-dianilinopyridine dihydrochloride (25.5 g, 92%). Anal. Calcd. for C17H17N5.2HCl: C, 56.0; H, 5.2; N, 19.2; Cl, 19.5. Found: C, 54.0; H, 5.4; N, 19.4; Cl, 20.0.

Aufarbeitung

  1. temperatureThe combined reduction mixtures were cooled
  2. customprecipitated product and catalyst
  3. filtrationfiltered under nitrogen
  4. washthe filter cake washed with 10% HCl in isopropyl alcohol
  5. additionThe filter cake was added to 500 ml
  6. filtrationfiltered
  7. washthe insolubles washed with conc. HCl
  8. temperatureThe clear filtrate was cooled (0°C)
  9. additiondiluted with 500 ml cold (-15°C) isopropyl alcohol
  10. stirringwith good stirring
  11. customto precipitate product
  12. filtrationThe solid was filtered
  13. washwashed with 10% HCl in isopropyl alcohol and vacuum
  14. dry with materialdried over P2O5

Quellen und Nachweise

ORD-Eintrag
ord-434c5fd0ece249f686f0282c8de3ef5c
Quelldatensatz
uspto-grants-1976_03
Patentnummer
US03943125

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