Phosphorus tribromide → (+/-)-trans-2-Bromo-6-propyl-5,5a,6,7,8,9,9a,10-octahydropyrido[2,3-g]quinoline dihydrobromide

HRID 2165266Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2165266
P(Br)(Br)[Br:2].O=[C:6]1[NH:22][C:10]2[CH2:11][C@H:12]3[C@H:17]([CH2:18][C:9]=2[CH:8]=[CH:7]1)[N:16]([CH2:19][CH2:20][CH3:21])[CH2:15][CH2:14][CH2:13]3>CN(C)C=O>[BrH:2].[BrH:2].[Br:2][C:6]1[CH:7]=[CH:8][C:9]2[CH2:18][C@H:17]3[C@@H:12]([CH2:13][CH2:14][CH2:15][N:16]3[CH2:19][CH2:20][CH3:21])[CH2:11][C:10]=2[N:22]=1

Komponenten

4

Edukt 2

HCID 24614Phosphorus tribromideHCID 18640067(+/-)-trans-2-Oxo-6-propyl-1,2,5,5a,6,7,8,9,9a,10-decahydropyrido[2,3-g]quinoline

Produkt 1

HCID 18640060(+/-)-trans-2-Bromo-6-propyl-5,5a,6,7,8,9,9a,10-octahydropyrido[2,3-g]quinoline dihydrobromideAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Phosphorus tribromide (30.7 mL, 87.5 g, 324 mMol) was added dropwise over 22 hours to a solution of (±)-trans-2-oxo-6-propyl-1,2,5,5a,6,7,8,9,9a,10-decahydropyrido[2,3-g]quinoline (1.50 g, 6.06 mMol) in dimethylformamide (100 mL) at 100° C. The reaction was quenched by the dropwise addition of water (50 mL). This mixture was poured over ice and made basic by addition of NH4OH and extracted with methylene chloride. The extract was dried (Na2SO4) and concentrated to give a brown oil. Purification by flash chromatography (7% methanol in methylene chloride, 0.5% NH4OH) gave the desired product as an orange oil (Rf=0.54, 1.22 g, 65% yield).

Aufarbeitung

  1. customThe reaction was quenched by the dropwise addition of water (50 mL)
  2. additionThis mixture was poured over ice
  3. additionmade basic by addition of NH4OH
  4. extractionextracted with methylene chloride
  5. dry with materialThe extract was dried (Na2SO4)
  6. concentrationconcentrated
  7. customto give a brown oil
  8. customPurification by flash chromatography (7% methanol in methylene chloride, 0.5% NH4OH)

Quellen und Nachweise

ORD-Eintrag
ord-d385a6a8ee104193b58ad7c49dd1b487
Quelldatensatz
uspto-grants-1990_07
Patentnummer
US04939259

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