2-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline → N-(2-Amino-5-nitro-phenyl)-2-(4-ethoxy-phenyl)-acetamide

HRID 2074457Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2074457
[N+:1]([C:4]1[CH:5]=[C:6]([NH2:11])[C:7]([NH2:10])=[CH:8][CH:9]=1)([O-:3])=[O:2].[CH2:12]([O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22](O)=[O:23])=[CH:17][CH:16]=1)[CH3:13].C(OC1C=CC2C(=CC=CC=2)N1C(OCC)=O)C>CN(C)C=O>[NH2:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]=1[NH:11][C:22](=[O:23])[CH2:21][C:18]1[CH:19]=[CH:20][C:15]([O:14][CH2:12][CH3:13])=[CH:16][CH:17]=1

Komponenten

5

Edukt 3

HCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 78631Benzeneacetic acid, 4-ethoxy-HCID 51117914-Nitro-1,2-phenylenediamine

Produkt 1

HCID 59799754N-(2-Amino-5-nitro-phenyl)-2-(4-ethoxy-phenyl)-acetamideAusbeute 67,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

4-Nitro-benzene-1,2-diamine 40 (1.00 g, 6.53 mmol) was dissolved in anhydrous dimethylformamide (20 mL) in a small, argon purged flask fitted with an condenser and magnetic stirbar. (4-Ethoxy-phenyl)-acetic acid 5 (1.53 g, 8.49 mmol) followed by 2-Ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline (2.099 g, 8.49 mmol) are added quickly as solids and resulting solution heated in an oil bath at 100° C. for 17 hours. After cooling to room temperature the solution was diluted with ice cold H2O (25 mL) resulting in the formation of a yellow precipitate that was collected on a sintered glass funnel and washed with H2O. The solid was slurried in boiling ethanol, filtered and dried to yield solid 41 N-(2-Amino-5-nitro-phenyl)-2-(4-ethoxy-phenyl)-acetamide Yield: 1.31 grams (67.5%). 1H NMR (DMSO) δ: 1.31 (t, 3H, J=6.9), 3.61 (s, 2H), 4.00 (q, 2H, J=6.9), 6.50 (br s, 2H, exchange w. D2O), 6.75 (d, 1H, J=9.0), 6.87 (d, 2H, J=8.4), 7.25 (d, 2H, J=8.7), 7.84 (dd, 1H, J=9.0, 2.7), 8.20 (d, 1H, J=2.7), 9.37 (br s, 1H, exchange w. D2O); MS (APCI+): 316 (MH+, 10%), 298 (MH+-H2O, 100%).

Aufarbeitung

  1. customfitted with an condenser
  2. additionare added quickly as solids
  3. customresulting solution
  4. temperatureAfter cooling to room temperature the solution
  5. customresulting in the formation of a yellow precipitate that
  6. customwas collected on a sintered glass funnel
  7. washwashed with H2O
  8. filtrationfiltered
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-ea3b592121b4406d9d3746381857d857
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07919510B2

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