Ammonium Hydroxide → 3,5-Diamino-4-methylbenzonitrile

HRID 861929Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 861929
[C:1]([C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[C:6]([CH3:12])=[C:5]([N+:13]([O-])=O)[CH:4]=1)#[N:2].[Sn].[OH-].[NH4+]>Cl.C(O)(=O)C>[C:1]([C:3]1[CH:4]=[C:5]([NH2:13])[C:6]([CH3:12])=[C:7]([NH2:9])[CH:8]=1)#[N:2]

Komponenten

6

Edukt 3

HCID 14923Ammonium HydroxideHCID 51343164-Methyl-3,5-dinitrobenzonitrileHCID 5352426Tin atom

Produkt 1

HCID 184653753,5-Diamino-4-methylbenzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 313Hydrochloric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A solution of 4-cyano-2,6-dinitrotoluene (8.55 g) in concentrated hydrochloric acid (70 mL) and glacial acetic acid (10 mL) is treated with tin metal (granules, 14.66 g), which is added slowly so that the temperature does not exceed 50° C. The reaction is stirred at 50° C. for 2.5 hours, then poured into ice and basified to pH=11 with concentrated ammonium hydroxide. The products are extracted with ethyl acetate (5×300 mL). The combined extracts are dried over sodium sulfate and rotary evaporated. The residue is purified by flash chromatography on silica gel, eluting with 50% ethyl acetate/hexane to afford 4-cyano-2,6-diaminotoluene as a yellow solid.

Aufarbeitung

  1. additionis added slowly so that the temperature
  2. customdoes not exceed 50° C
  3. extractionThe products are extracted with ethyl acetate (5×300 mL)
  4. dry with materialThe combined extracts are dried over sodium sulfate and rotary evaporated
  5. customThe residue is purified by flash chromatography on silica gel
  6. washeluting with 50% ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-6953c60b594a4eb9a7ee139aa7b12d0c
Quelldatensatz
uspto-grants-1998_02
Patentnummer
US05716966

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