StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

2-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline → N-[2-(2-Diethylaminoethylamino)-5-nitro-phenyl]-2-(4-ethoxyphenyl)acetamide

HRID 2074444
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2074444
[CH2:1]([N:3]([CH2:17][CH3:18])[CH2:4][CH2:5][NH:6][C:7]1[C:8]([NH2:16])=[CH:9][C:10]([N+:13]([O-:15])=[O:14])=[CH:11][CH:12]=1)[CH3:2].[CH2:19]([O:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29](O)=[O:30])=[CH:24][CH:23]=1)[CH3:20].C(OC1C=CC2C(=CC=CC=2)N1C(OCC)=O)C>ClCCl>[CH2:17]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][NH:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:8]=1[NH:16][C:29](=[O:30])[CH2:28][C:25]1[CH:26]=[CH:27][C:22]([O:21][CH2:19][CH3:20])=[CH:23][CH:24]=1)[CH3:18]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 78631Benzeneacetic acid, 4-ethoxy-HCID 98378961-N-[2-(diethylamino)ethyl]-4-nitrobenzene-1,2-diamine

Produkt 1

HCID 4405038N-[2-(2-Diethylaminoethylamino)-5-nitro-phenyl]-2-(4-ethoxyphenyl)acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344Dichloromethane
Lösungsmittel

Reaktionsbedingungen

Temperatur
35 °C

Versuchsvorschrift

N1-(2-Diethylamino-ethyl)-4-nitro-benzene-1,2-diamine 4a (0.47 g, 1.863 mmol) was dissolved in anhydrous dichloromethane (110 mL) in a small, argon purged flask fitted with an condenser and magnetic stirbar. (4-Ethoxy-phenyl)-acetic acid 5 (0.352 g, 1.956 mmol) followed by 2-Ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline (0.552 g, 2.235 mmol) are added quickly as solids and resulting solution heated in an oil bath at 35° C. for 18 hours. After cooling to room temperature the solvent was removed under reduced pressure and the resulting residue partitioned between H2O and chloroform and 3M ammonium hydroxide solution added to adjust pH to 11-12. The mixture was transferred to a separatory funnel and the organic layer collected. The aqueous layer was further extracted with chloroform and the combined organic layers were washed with brine, dried over magnesium sulphate, filtered and concentrated to afford crude solid. Recrystallization of the crude solid from ethyl acetate yielded a yellow powder 6a N-[2-(2-Diethylamino-ethylamino)-5-nitro-phenyl]-2-(4-ethoxy-phenyl)-acetamide. Yield: 0.305 grams (39.5%). 1H NMR (DMSO) δ: 0.94 (t, 6H, J=7.1), 1.31 (t, 3H, J=6.9), 2.50 (m, 4H), 2.59 (t, 2H, J=6.5), 3.26 (m, 2H), 3.55 (s, 2H), 4.02 (q, 2H, J=6.9), 6.21 (br s, 1H), 6.75 (d, 1H, J=9.9), 6.87 (d, 2H, J=8.4), 7.24 (d, 2H, J=8.4), 7.97 (m, 2H), 9.54 (br s, 1H); MS (ESI): 415 (MH+, 100%)

Aufarbeitung

  1. customfitted with an condenser
  2. additionare added quickly as solids
  3. customresulting solution
  4. temperatureAfter cooling to room temperature the solvent
  5. customwas removed under reduced pressure
  6. customthe resulting residue partitioned between H2O and chloroform and 3M ammonium hydroxide solution
  7. additionadded
  8. customThe mixture was transferred to a separatory funnel
  9. customthe organic layer collected
  10. extractionThe aqueous layer was further extracted with chloroform
  11. washthe combined organic layers were washed with brine
  12. dry with materialdried over magnesium sulphate
  13. filtrationfiltered
  14. concentrationconcentrated
  15. customto afford crude solid
  16. customRecrystallization of the crude solid from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-933be93d936e4f0d8e8c54261b540042
Quelldatensatz
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07919510B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion