Methylamine → N~2~-Methyl-4-nitrobenzene-1,2-diamine

HRID 2213119Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2213119
F[C:2]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:3]=1N.[CH3:12][NH2:13].C1COCC1.C(=O)([O-])[O-].[K+].[K+].C[N:26]1CCCC1=O>>[CH3:12][NH:13][C:3]1[C:2]([NH2:26])=[CH:8][CH:7]=[C:6]([N+:9]([O-:11])=[O:10])[CH:5]=1

Komponenten

6

Edukt 5

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 677852-Fluoro-5-nitroaniline

Produkt 1

HCID 21956374N~2~-Methyl-4-nitrobenzene-1,2-diamine

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

In a 350 mL pressure flask, 2-fluoro-5-nitroaniline (10 g, 0.064 mol), methylamine as a 2M solution in THF (65 mL, 0.13 mol) and potassium carbonate (18 g, 0.13 mol) in 1-Methyl-2-pyrrolidinone (80 mL) were combined. The flask was sealed and heated to 120 degrees C. overnight. The reaction was monitored by TLC. When reaction was judged to be complete based upon consumption of 2-fluoro-5-nitroaniline, it was cooled to room temperature and poured into 2–3 times the total reaction volume of water. When a precipitate was formed, it was filtered and dried. The product was carried on without purification. 1H NMR (300 MHz, d6DMSO) δ 7.54 (dd, J=8.79, 2.64 Hz, 1H), 7.39 (d, J=2.64 Hz, 1H), 6.41 (d, J=8.79 Hz, 1H), 6.11 (d, J=4.39 Hz, 1H), 5.07 (s, 2H), 2.83 (d, J=4.83 Hz, 3H).

Aufarbeitung

  1. customThe flask was sealed
  2. customovernight
  3. customWhen reaction
  4. customto be complete based upon consumption of 2-fluoro-5-nitroaniline, it
  5. temperaturewas cooled to room temperature
  6. additionpoured into 2–3 times the total reaction volume of water
  7. customWhen a precipitate was formed
  8. filtrationit was filtered
  9. customdried
  10. customThe product was carried on without purification

Quellen und Nachweise

ORD-Eintrag
ord-453685f1a9514f94977ac8bcda06111e
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07105530B2

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