Morpholine → 2-(2-Morpholinoethoxy)-6-nitroaniline

HRID 415110Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 415110
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[C:6]=1[NH2:7].[NH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1>CC(N(C)C)=O>[O:18]1[CH2:19][CH2:20][N:15]([CH2:2][CH2:3][O:4][C:5]2[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[C:6]=2[NH2:7])[CH2:16][CH2:17]1

Komponenten

4

Edukt 2

HCID 8083MorpholineHCID 111719662-(2-Chloro-ethoxy)-6-nitro-phenylamine

Produkt 1

HCID 593495682-(2-Morpholinoethoxy)-6-nitroaniline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

2-(2-Chloroethoxy)-6-nitroaniline (1.9 g, 4.63 mmol), morpholine (0.5 mL) was dissolved in 5 mL of DMA. The mixture was heated at 110° C. in a pressure bottle overnight, and then cooled to room temperature. The reaction mixture was separated between ethyl acetate and water, the combined organic layers were washed with water, brine, dried, and concentrated to get 1.3 g of 2-(2-Morpholinoethoxy)-6-nitroaniline, which was used without any further purification. 1H-NMR (400 MHz, CDCl3): δ 7.78 (d, 1H), 6.95 (d, 1H), 6.72 (b, 2H), 6.61 (dd, 1H), 4.16 (t, 2H), 3.75 (t, 2H), 2.82 (m, 2H), 2.58 (m, 4H), 2.10 (m, 2H). MS (EI): 263 (MH+).

Aufarbeitung

  1. temperaturecooled to room temperature
  2. customThe reaction mixture was separated between ethyl acetate and water
  3. washthe combined organic layers were washed with water, brine
  4. customdried
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-5acbcab4f92d4bfab01f4b14c7d008d8
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088767B2

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