Tetrahydrofuran → (2-Fluoro-4-nitrophenyl)methanamine

HRID 1428785Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1428785
[F:1][C:2]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:3]=1[CH2:4][N:5]1C(=O)C2C(=CC=CC=2)C1=O.O1CCCC1>>[F:1][C:2]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:3]=1[CH2:4][NH2:5]

Komponenten

3

Edukt 2

HCID 8028TetrahydrofuranHCID 708476692-(2-Fluoro-4-nitrobenzyl)isoindoline-1,3-dione

Produkt 1

HCID 45121148(2-Fluoro-4-nitrophenyl)methanamineAusbeute 41,5 %

Versuchsvorschrift

To a solution of 2-(2-fluoro-4-nitrobenzyl)isoindoline-1,3-dione (1.35 g, 4.48 mmol) in tetrahydrofurane 65% hydrazine monohydrate (1.3 mL, 4 eq) was added. The mixture was refluxed for 6 h. After the starting material was consumed, the mixture was cooled down to room temperature and treated with potassium bicarbonate to pH 12˜13. Then it was extracted with ethyl acetate and washed with brine. Drying over magnesium sulfate, evaporation of the ethyl acetate and purification by column chromatography gave (2-fluoro-4-nitrophenyl)methanamine (316 mg, 41%).

Aufarbeitung

  1. temperatureThe mixture was refluxed for 6 h
  2. customAfter the starting material was consumed
  3. additiontreated with potassium bicarbonate to pH 12˜13
  4. extractionThen it was extracted with ethyl acetate
  5. washwashed with brine
  6. dry with materialDrying over magnesium sulfate, evaporation of the ethyl acetate and purification by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-6743afb4006145d99b249d262d228b6e
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08937092B2

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