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

HRID 1110704Notes

Reaction equation

HRID 1110704 reaction equation
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

Participants

4

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-1b0a53bb39be4be188fc1a09ca291899
Source dataset
uspto-grants-1990_12
Patent number
US04977149

Reaction notes

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