Hydrazine hydrate (1:1) → 2-amino-3-benzyloxy-N-methylaniline

HRID 636484Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 636484
[CH2:1]([O:8][C:9]1[C:10]([N+:17]([O-])=O)=[C:11]([CH:14]=[CH:15][CH:16]=1)[NH:12][CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.NN>CO>[NH2:17][C:10]1[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:16][CH:15]=[CH:14][C:11]=1[NH:12][CH3:13]

Komponenten

4

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 107298903-benzyloxy-2-nitro-N-methylaniline

Produkt 1

HCID 104895412-amino-3-benzyloxy-N-methylanilineAusbeute 87,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a mixture of 3-benzyloxy-N-methyl-2-nitroaniline (453.3 mg), 80% methanol (6.8 ml), anhydrous ferric chloride (13.6 mg) and carbon (13.6 mg) was dropwise added hydrazine monohydrate (255.6 μl), and the mixture was stirred for 5 hours at ambient temperature. Insoluble material was filtered off, and the filtrate was concentrated in vacuo. To the residue were added ethyl acetate and saturated sodium bicarbonate solution, and the separated organic layer was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by silica gel column chromatography (ethyl acetate—n-hexane) to give 2-amino-3-benzyloxy-N-methylaniline (348.9 mg).

Aufarbeitung

  1. filtrationInsoluble material was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. additionTo the residue were added ethyl acetate and saturated sodium bicarbonate solution
  4. washthe separated organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate—n-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-a7ec7bb27e934f0e9e61ba5a67f5aef6
Quelldatensatz
uspto-grants-2001_02
Patentnummer
US06194396B1

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