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Methanol → 1-Acetamido-4-bromo-2-nitro-7-pyrrolidin-1-yl-5,6,7,8-tetrahydronaphthalene

HRID 863523
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 863523
[C:1]([NH:4][C:5]1[C:14]2[CH2:13][CH:12]([N:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)[CH2:11][CH2:10][C:9]=2[C:8]([Br:20])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[N+:21]([O-])([OH:23])=[O:22].CCOC(C)=O.CO>FC(F)(F)C(O)=O>[C:1]([NH:4][C:5]1[C:14]2[CH2:13][CH:12]([N:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)[CH2:11][CH2:10][C:9]=2[C:8]([Br:20])=[CH:7][C:6]=1[N+:21]([O-:23])=[O:22])(=[O:3])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 887MethanolHCID 944Nitric AcidHCID 8857Ethyl AcetateHCID 196962081-Acetamido-4-bromo-7-pyrrolidin-1-yl-5,6,7,8-tetrahydronaphthalene

Produkt 1

HCID 196962571-Acetamido-4-bromo-2-nitro-7-pyrrolidin-1-yl-5,6,7,8-tetrahydronaphthalene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422
Trifluoroacetic acid
Lösungsmittel

Versuchsvorschrift

A mixture of 1-acetamido-4-bromo-7-pyrrolidin-1-yl-5,6,7,8-tetrahydronaphthalene (0.3 g) in trifluoroacetic acid (10 mL) was cooled in an icebath and treated with fuming nitric acid (0.5 mL). After stirring for 4 h, the solvent was evaporated and the residue taken up in methylene chloride:water. The mixture was basified with 12.5% NaOH, and the aqueous layer back extracted. The combined organic layers were dried over sodium sulfate, filtered and evaporated to give a solid. Preparative thin layer chromatography (7:3 EtOAc:MeOH) was used to obtain the purified product (0.12 g).

Aufarbeitung

  1. temperaturewas cooled in an icebath
  2. customthe solvent was evaporated
  3. extractionthe aqueous layer back extracted
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto give a solid

Quellen und Nachweise

ORD-Eintrag
ord-a4b05536447847489ca020887ff9e7f9
Quelldatensatz
uspto-grants-1998_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05721234

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