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Isoamyl Nitrite → 1-[11-(2-Ethylhexyl)-5-(2,4,6-trimethylbenzoyl)-11H-benzo[a]carbazol-8-yl]-2-phenyl ethane-1,2-dione 2-oxime

HRID 2172365
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2172365
[CH2:1]([CH:3]([CH2:42][CH2:43][CH2:44][CH3:45])[CH2:4][N:5]1[C:17]2[C:12](=[CH:13][C:14]([C:22](=[O:32])[C:23]3[C:28]([CH3:29])=[CH:27][C:26]([CH3:30])=[CH:25][C:24]=3[CH3:31])=[C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]3=2)[C:11]2[C:6]1=[CH:7][CH:8]=[C:9]([C:33](=[O:41])[CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH:10]=2)[CH3:2].[N:46](OCCC(C)C)=[O:47]>C1COCC1>[CH2:1]([CH:3]([CH2:42][CH2:43][CH2:44][CH3:45])[CH2:4][N:5]1[C:17]2[C:12](=[CH:13][C:14]([C:22](=[O:32])[C:23]3[C:24]([CH3:31])=[CH:25][C:26]([CH3:30])=[CH:27][C:28]=3[CH3:29])=[C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]3=2)[C:11]2[C:6]1=[CH:7][CH:8]=[C:9]([C:33](=[O:41])[C:34]([C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)=[N:46][OH:47])[CH:10]=2)[CH3:2]
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Komponenten

4

Edukt 2

HCID 8053Isoamyl NitriteHCID 866905311-[11-(2-Ethylhexyl)-5-(2,4,6-trimethylbenzoyl)-11H-benzo[a]carbazol-8-yl]-2-phenyl ethanone

Produkt 1

HCID 866905321-[11-(2-Ethylhexyl)-5-(2,4,6-trimethylbenzoyl)-11H-benzo[a]carbazol-8-yl]-2-phenyl ethane-1,2-dione 2-oximeAusbeute 54,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The mixture of 1-[11-(2-Ethylhexyl)-5-(2,4,6-trimethylbenzoyl)-11H-benzo[a]carbazol-8-yl]-2-phenyl ethanone (1.20 g, 2.03 mmol) and isoamyl nitrite (0.50 g, 4.26 mmol) in THF (6 ml) is bubbled with HCl gas for 1 minute. After stirring at room temperature for 4 hours, the reaction mixture is poured into ice-water. The crude product is extracted with CH2Cl2, and washed with water and brine. After drying over MgSO4 and concentration, the crude is purified by column chromatography on silica gel eluting with a mixed solvent of n-hexane and CH2Cl2 (1:1) to obtain an off-white resin (0.69 g, 50%). The structure is confirmed by 1H-NMR spectrum (CDCl3) δ [ppm]: 0.79-0.90 (m), 1.19-1.45 (m), 2.19 (s), 2.28 (m), 2.42 (s), 4.75 (m), 6.97 (s), 7.35-7.41 (m), 7.57 (d), 7.63 (d), 7.70-7.79 (m), 7.98 (d), 8.35 (s), 8.63 (d), 8.72 (s), 9.54 (d).

Aufarbeitung

  1. customis bubbled with HCl gas for 1 minute
  2. additionthe reaction mixture is poured into ice-water
  3. extractionThe crude product is extracted with CH2Cl2
  4. washwashed with water and brine
  5. dry with materialAfter drying over MgSO4 and concentration
  6. customthe crude is purified by column chromatography on silica gel eluting with a mixed solvent of n-hexane and CH2Cl2 (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-dcd9d12a2aba455d919bcc2d1fc12df9
Quelldatensatz
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09051397B2

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