Nitric Acid → 4-Fluoro-2-methyl-5-nitroaniline

HRID 599335Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 599335
[N+:1]([O-:4])(O)=[O:2].[F:5][C:6]1[CH:12]=[CH:11][C:9]([NH2:10])=[C:8]([CH3:13])[CH:7]=1>OS(O)(=O)=O>[F:5][C:6]1[C:12]([N+:1]([O-:4])=[O:2])=[CH:11][C:9]([NH2:10])=[C:8]([CH3:13])[CH:7]=1

Komponenten

4

Edukt 2

HCID 944Nitric AcidHCID 679824-Fluoro-2-methylaniline

Produkt 1

HCID 190352714-Fluoro-2-methyl-5-nitroanilineAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

Concentrated nitric acid (17 g, 0.18 mol) was added dropwise to a stirred solution of 4-fluoro-2-methylaniline (20 g, 0.16 mol) in cone H2SO4 (300 mL) at −10° C. The mixture was stirred at −10° C. for 10 min., and the reaction mixture was poured into ice water. The resultant solid was collected by filtration and partitioned between EtOAc and aq Na2CO3 solution (pH 8). The organic solution was washed with brine, dried (MgSO4) and concentrated to give 4-fluoro-2-methyl-5-nitroaniline (20 g, 74% yield). 1H NMR (400 MHz, DMSO-d6): δ 7.27 (d, J=6.8 Hz, 1 H), 7.14 (d, J=12.4 Hz, 1 H) 5.37 (s, 2 H), 2.10 (s, 3 H).

Aufarbeitung

  1. filtrationThe resultant solid was collected by filtration
  2. custompartitioned between EtOAc and aq Na2CO3 solution (pH 8)
  3. washThe organic solution was washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-2d38e53abfed40418e574501f432404f
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07897762B2

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