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Ammonium Chloride → 8-Amino-4-(4-chloro-5-methoxy-2-methylanilino)[1]benzothieno[3,2-b]pyridine-3-carbonitrile

HRID 989325
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 989325
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([NH:10][C:11]2[C:16]([C:17]#[N:18])=[CH:15][N:14]=[C:13]3[C:19]4[CH:25]=[C:24]([N+:26]([O-])=O)[CH:23]=[CH:22][C:20]=4[S:21][C:12]=23)=[C:4]([CH3:29])[CH:3]=1.[Cl-].[NH4+]>CO.[Fe]>[NH2:26][C:24]1[CH:23]=[CH:22][C:20]2[S:21][C:12]3[C:13](=[N:14][CH:15]=[C:16]([C:17]#[N:18])[C:11]=3[NH:10][C:5]3[CH:6]=[C:7]([O:8][CH3:9])[C:2]([Cl:1])=[CH:3][C:4]=3[CH3:29])[C:19]=2[CH:25]=1
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Komponenten

5

Edukt 2

HCID 25517Ammonium Chloride2×HCID 219564974-(4-Chloro-5-methoxy-2-methylphenylamino)-8-nitrobenzo[4,5]thieno[3,2-b]pyridine-3-carbonitrile

Produkt 1

HCID 219564408-Amino-4-(4-chloro-5-methoxy-2-methylanilino)[1]benzothieno[3,2-b]pyridine-3-carbonitrileAusbeute 37,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysator2×
HCID 887
Methanol
Lösungsmittel

Versuchsvorschrift

A mixture of 476 mg (1.12 mmol) of 4-(4-chloro-5-methoxy-2-methylphenylamino)-8-nitrobenzo[4,5]thieno[3,2-b]pyridine-3-carbonitrile, 180 mg (3.22 mmol) of iron powder and 180 mg (3.36 mmol) of ammonium chloride in 20 mL of 50% aqueous methanol is heated at reflux temperature for 2 hours. An additional 80 mg (1.42 mmol) of iron powder and 100 mg (1.87 mmol) of ammonium chloride are added and the reaction mixture is heated at reflux temperature for 2 hours, then stirred at room temperature overnight. The reaction mixture is heated at reflux for 4 hours then cooled slightly and filtered. The solid residue is extracted with several portions of hot ethyl acetate followed by hot methanol. All the organic layers are combined and washed with water. The organic layer is dried over magnesium sulfate, filtered and concentrated in vacuo. The residue is purified by flash chromatography eluting with a gradient of 1:1 hexane/ethyl acetate to only ethyl acetate to give 165 mg (37%) of a tan solid, mp 266-268° C. dec.

Aufarbeitung

  1. temperatureis heated
  2. temperatureat reflux temperature for 2 hours
  3. temperaturethe reaction mixture is heated
  4. temperatureat reflux temperature for 2 hours
  5. temperatureThe reaction mixture is heated
  6. temperatureat reflux for 4 hours
  7. temperaturethen cooled slightly
  8. filtrationfiltered
  9. extractionThe solid residue is extracted with several portions of hot ethyl acetate
  10. washwashed with water
  11. dry with materialThe organic layer is dried over magnesium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated in vacuo
  14. customThe residue is purified by flash chromatography
  15. washeluting with a gradient of 1:1 hexane/ethyl acetate to only ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-b10afad84aec48a89af3e78969c5fc45
Quelldatensatz
uspto-grants-2003_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06638929B2

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