1,3-Dibromopropane → HCID 12992363, compound

HRID 2180936Notes

Reaction equation

HRID 2180936 reaction equation
[H-].[Na+].[NH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][C:4]1=[O:13].[Br:14][CH2:15][CH2:16][CH2:17]Br>CN(C)C=O>[Br:14][CH2:15][CH2:16][CH2:17][N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][C:4]1=[O:13]

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 24758Sodium hydrideHCID 64796Hydrocarbostyril

Product 1

HCID 12992363HCID 12992363, compoundYield 59.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A suspension of sodium hydride (6.8 g, 60% in mineral oil) and dimethyl formamide (200 mL) was kept at 20-25° C. followed by the addition of a solution of 3,4-dihydroquinolin-2(1H)-one (25.0 g) in dimethyl formamide (180 mL). The resulting mixture was stirred at room temperature for 10 min followed by the addition of a solution of 1,3-dibromopropane (172 g) in dimethyl formamide (150 mL) at a temperature of 20-35° C. The resulting mixture was stirred at 30° C. for 20 min and concentrated in vacuo. The residue was poured onto ice, and the aqueous phase was extracted with ethyl acetate. The combined organic phases were washed with brine, dried (MgSO4) and concentrated in vacuo. The crude product was purified by flash chromatography on silicagel (eluent:ethyl acetate/heptane 1:1) to give the product as a yellow oil (27 g).

Workup

  1. customwas kept at 20-25° C.
  2. stirringThe resulting mixture was stirred at 30° C. for 20 min
  3. concentrationconcentrated in vacuo
  4. additionThe residue was poured onto ice
  5. extractionthe aqueous phase was extracted with ethyl acetate
  6. washThe combined organic phases were washed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by flash chromatography on silicagel (eluent:ethyl acetate/heptane 1:1)

Sources & evidence

ORD record
ord-aaa0ded27b7f40bdaa34ba1438250ba6
Source dataset
uspto-grants-2005_05
Patent number
US06890916B2

Reaction notes

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