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Dimethylformamide → 4-([2-(4-Chlorobutyrylamino)-4-pyridyl]oxy)aniline

HRID 1010205
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1010205
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[Cl:18][CH2:19][CH2:20][CH2:21][C:22](Cl)=[O:23].C(N(CC)CC)C.CN(C)C=O>O1CCCC1>[Cl:18][CH2:19][CH2:20][CH2:21][C:22]([NH:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)[CH:5]=[CH:4][N:3]=1)=[O:23]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 783704-Chlorobutyryl chlorideHCID 229367164-(4-Nitrophenoxy)pyridin-2-amine

Produkt 1

HCID 579333274-([2-(4-Chlorobutyrylamino)-4-pyridyl]oxy)aniline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

2-Amino-4-(4-nitrophenoxy)pyridine (300 mg), 4-chlorobutyryl chloride (0.18 ml), triethylamine (0.77 ml), dimethylformamide (1 ml) and tetrahydrofuran (1 ml) were stirred at room temperature for 10 minutes, and then silica gel was added to the reaction solution, the solvent was distilled off under reduced pressure and the reaction product was adsorbed onto the silica gel. The silica gel was charged into a dry column packed with silica gel, for column purification (hexane:ethyl acetate=3:1, followed by 2:1 and 1:1). The solvent was distilled off under reduced pressure, and then 300 mg of iron powder, 600 mg of ammonium chloride, 2 ml of DMF, 1 ml of ethanol and 1 ml of water were added to 150 mg of the resulting residue and the mixture was stirred at 100° C. for 20 minutes. After filtration with celite, water and ethyl acetate were added for extraction. The organic layer was washed 5 times with aqueous ammonium chloride solution and then dried over magnesium sulfate. The drying agent was filtered off and the solvent was distilled off under reduced pressure to obtain 110 mg of the target substance as an oil.

Aufarbeitung

  1. additionsilica gel was added to the reaction solution
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionThe silica gel was charged into a dry column
  4. custompacked with silica gel, for column purification (hexane:ethyl acetate=3:1, followed by 2:1 and 1:1)
  5. distillationThe solvent was distilled off under reduced pressure
  6. addition300 mg of iron powder, 600 mg of ammonium chloride, 2 ml of DMF, 1 ml of ethanol and 1 ml of water were added to 150 mg of the resulting residue
  7. filtrationAfter filtration with celite, water and ethyl acetate
  8. additionwere added for extraction
  9. washThe organic layer was washed 5 times with aqueous ammonium chloride solution
  10. dry with materialdried over magnesium sulfate
  11. filtrationThe drying agent was filtered off
  12. distillationthe solvent was distilled off under reduced pressure
  13. customto obtain 110 mg of the target substance as an oil

Quellen und Nachweise

ORD-Eintrag
ord-5dadfb246c154cca864fa39594943baf
Quelldatensatz
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07973160B2

Notizen zur Reaktion

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