Acetic Acid → HCID 59303232, Verbindung

HRID 2238390Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2238390
[Cl:1][CH2:2][CH:3]1[C:11]2[C:10]3[C:12]([N+:16]([O-:18])=[O:17])=[CH:13][CH:14]=[CH:15][C:9]=3[CH:8]=[CH:7][C:6]=2[N:5](C(=O)C(F)(F)F)[CH2:4]1.C([O-])([O-])=O.[Cs+].[Cs+].CC(O)=O>O1CCOCC1.O.CO>[Cl:1][CH2:2][CH:3]1[C:11]2[C:10]3[C:12]([N+:16]([O-:18])=[O:17])=[CH:13][CH:14]=[CH:15][C:9]=3[CH:8]=[CH:7][C:6]=2[NH:5][CH2:4]1

Komponenten

7

Edukt 3

HCID 176Acetic AcidHCID 10796Cesium carbonateHCID 44549147HCID 44549147, Verbindung

Produkt 1

HCID 59303232HCID 59303232, VerbindungAusbeute 91,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of 132 (1.54 g, 4.29 mmol) in dioxane (10 mL) was treated with a solution of Cs2CO3 (3.26 g, 10 mmol) in water (3 mL) and MeOH (7 mL) and the mixture was stirred at room temperature for 10 min. The mixture was treated with AcOH (12 mL), then concentrated under reduced pressure to a small volume and partitioned between water and CHCl2. The organic phase was washed with water (×2), dried, and filtered through a column of silica gel. The resulting oil was crystallised from EtOAc/petroleum ether to give 1-(chloromethyl)-9-nitro-1,2-dihydro-3H-benzo[e]indole (136) (1.03 g, 91%) as a red solid: mp 100° C.; 1H NMR [(CD3)2SO] δ 8.07 (dd, J=8.0, 1.1 Hz, 1H), 7.94 (dd, J=7.6, 1.3 Hz, 1H), 7.87 (d, J=8.7H, 1H), 7.21 (t, J=7.8 Hz, 1H), 7.13 (d, J=8.7 Hz, 1H), 6.63 (s, 1H), 3.81-3.71 (m, 1H), 3.71-3.62 (m, 1H), 3.62-3.54 (m, 1H), 3.33-3.25 (m, 2H). Anal. (C13H11ClN2O2) C, H, N.

Aufarbeitung

  1. concentrationconcentrated under reduced pressure to a small volume
  2. custompartitioned between water and CHCl2
  3. washThe organic phase was washed with water (×2)
  4. customdried
  5. filtrationfiltered through a column of silica gel
  6. customThe resulting oil was crystallised from EtOAc/petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-64565ee67ceb453286903c32591b1f7c
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07718688B2

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