Ammonia → N-benzyl-6,7-dihydro-2-nitro-5H-benzocyclohepten-7-amine

HRID 274056Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 274056
[CH2:1]([NH:8][CH:9]1[CH2:15][CH2:14][C:13]2[CH:16]=[CH:17][C:18]([N+:20]([O-:22])=[O:21])=[CH:19][C:12]=2[CH:11](O)[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)[O-].[K+].O.N>ClCCl>[CH2:1]([NH:8][CH:9]1[CH:10]=[CH:11][C:12]2[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:13]=2[CH2:14][CH2:15]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 222AmmoniaHCID 962WaterHCID 516920Potassium bisulfateHCID 200948137-benzylamino-3-nitro-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-ol

Produkt 1

HCID 20094725N-benzyl-6,7-dihydro-2-nitro-5H-benzocyclohepten-7-amineAusbeute 50,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
210 °C

Versuchsvorschrift

A mixture of 7-benzylamino-3-nitro-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-ol (6.51 g) and potassium bisulfate (13.0 g) was heated at 210° C. for 20 minutes and suspended in a mixture of dichloromethane (150 ml), water (100 ml), and 28% ammonia solution. The suspension was filtered. The dichloromethane layer was separated, dried over magnesium sulfate, evaporated in vacuo, and chromatographed over silica gel using dichloromethane-methanol as an eluent. The first eluate afforded N-benzyl-6,7-dihydro-2-nitro-5H-benzocyclohepten-7-amine (3.11 g) as a dark brown solid.

Aufarbeitung

  1. filtrationThe suspension was filtered
  2. customThe dichloromethane layer was separated
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customchromatographed over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-b9005add38994275b56f2ff92a0e5568
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05387710

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