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Oxalyl chloride → HCID 67165232, Verbindung

HRID 553013
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 553013
[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]([C:7]([N:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]([C:19](O)=[O:20])[CH2:11][CH2:10]2)=[O:8])=[CH:5][CH:4]=1.C(Cl)(=O)C(Cl)=O.C(N(C(C)C)CC)(C)C.[Cl:39][C:40]1[CH:48]=[CH:47][C:43]([NH:44][CH2:45][CH3:46])=[CH:42][CH:41]=1>C(Cl)Cl.CN(C)C=O.C(OCC)(=O)C>[Cl:39][C:40]1[CH:48]=[CH:47][C:43]([N:44]([CH2:45][CH3:46])[C:19]([CH:12]2[C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:9]([C:7](=[O:8])[C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:23][CH:22]=3)[CH2:10][CH2:11]2)=[O:20])=[CH:42][CH:41]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 5878414-Chloro-N-ethylbenzenamineHCID 67165918HCID 67165918, Verbindung

Produkt 1

HCID 67165232HCID 67165232, VerbindungAusbeute 29,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228
Dimethylformamide
Katalysator
HCID 6344DichloromethaneLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

1-(4-Methoxy-benzoyl)-1,2,3,4-tetrahydro-quinoline-4-carboxylic acid (approx. 1.47 mmol) was suspended in methylene chloride (10 mL) to which one drop of dimethylformamide was added. Oxalyl chloride (375 mg, 275 uL, 2.95 mmol) was added. Vigorous bubbling ensued, followed by dissolution of the starting material. After stirring for 4 hours at room temperature, the yellow solution was concentrated and azeotroped with toluene to remove excess oxalyl chloride. The resulting acid chloride solution was dissolved in methylene chloride (10 mL). Diisopropylethylamine (569 mg, 768 uL, 4.41 mmol) was added, followed by 4-chloro-N-ethylaniline (457 mg, 2.93 mmol). The mixture was stirred at room temperature overnight. The reaction was poured into ethyl acetate and washed with water and brine. The combined organics were dried over sodium sulfate, filtered and concentrated. The crude residue was purified by silica gel chromatography (ethyl acetate/hexanes gradient) to afford (±)-1-(4-methoxy-benzoyl)-1,2,3,4-tetrahydro-quinoline-4-carboxylic acid (4-chloro-phenyl)-ethyl-amide (193 mg) as a foam. 1H-NMR (CDCl3) δ: 1.17 (t, 3H), 2.06-2.26 (m, 2H), 3.57-3.70 (m, 2H), 3.73-3.87 (m, 5H), 4.02 (dd, 1H), 6.52 (d, 1H), 6.66-6.74 (m, 2H), 6.84 (ddd, 1H), 6.93-7.06 (m, 2H), 7.17-7.24 (m, 2H), 7.37-7.43 (m, 2H). MS m/z: 449 (M+1).

Aufarbeitung

  1. additionwas added
  2. customVigorous bubbling
  3. dissolutionfollowed by dissolution of the starting material
  4. concentrationthe yellow solution was concentrated
  5. customazeotroped with toluene
  6. customto remove excess oxalyl chloride
  7. dissolutionThe resulting acid chloride solution was dissolved in methylene chloride (10 mL)
  8. stirringThe mixture was stirred at room temperature overnight
  9. washwashed with water and brine
  10. dry with materialThe combined organics were dried over sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customThe crude residue was purified by silica gel chromatography (ethyl acetate/hexanes gradient)

Quellen und Nachweise

ORD-Eintrag
ord-5e559d037304404c85d2868114cb6c6a
Quelldatensatz
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07951950B2

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