Nitric Acid → 1-(4-Fluoro-3-nitrophenyl)ethan-1-amine

HRID 58207Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 58207
[N+:1]([O-:4])(O)=[O:2].OS(O)(=O)=O.[F:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]([NH2:19])[CH3:18])=[CH:13][CH:12]=1.[OH-].[Na+]>>[F:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]([NH2:19])[CH3:18])=[CH:13][C:12]=1[N+:1]([O-:4])=[O:2]

Komponenten

5

Edukt 4

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 1230631-(4-Fluorophenyl)ethylamine

Produkt 1

HCID 552831001-(4-Fluoro-3-nitrophenyl)ethan-1-amineAusbeute 98 %

Versuchsvorschrift

Fuming HNO3 (0.48 ml, 10.8 mmol) was added carefully to ice bath cooled concentrated H2SO4 (3.6 ml, 68.2 mmol). To the mixture was added 1-(4-fluorophenyl)ethanamine (1.0 g, 7.2 mmol) dropwise. The reaction mixture was stirred with cooling for 50 minutes. The reaction mixture was poured into ice and basified with 3M NaOH solution (24 ml, 72.00 mmol) to about pH8.0. The alkaline solution was extracted with DCM twice. The combined organic layer was dried over Na2SO4 and evaporated to afford title compound (1.3 g, yield: 96%). 1H-NMR (400 MHz, CDCl3) δ 1.41 (d, 6H) 4.25 (q, 1H) 7.21-7.26 (m, 1H) 7.67 (ddd, 1H) 8.10 (dd, 1H)

Aufarbeitung

  1. temperaturewith cooling for 50 minutes
  2. extractionThe alkaline solution was extracted with DCM twice
  3. dry with materialThe combined organic layer was dried over Na2SO4
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-444c61759d80495580e7f0239ac9cf0b
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434697B2

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