2-Bromopropanoyl chloride → HCID 13051051, compound

HRID 620013Notes

Reaction equation

HRID 620013 reaction equation
[Br:1][CH:2]([CH3:6])[C:3](Cl)=[O:4].[CH3:7][N:8]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11][C:9]1=[O:10].[Al+3].[Cl-].[Cl-].[Cl-]>C(Cl)(Cl)Cl>[Br:1][CH:2]([CH3:6])[C:3]([C:15]1[CH:14]=[C:13]2[C:18](=[CH:17][CH:16]=1)[N:8]([CH3:7])[C:9](=[O:10])[CH2:11][CH2:12]2)=[O:4]

Participants

5

Reactant 3

HCID 979802-Bromopropanoyl chlorideHCID 5765131-Methyl-3,4-dihydroquinolin-2(1H)-oneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 13051051HCID 13051051, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-Bromopropionyl chloride (41.1 g) is added dropwise to a suspension of the N-methyl product obtained in Step 1. above (18.6 g) and AlCl3 (37.4 g) in chloroform (350 ml). The stirred reaction mixture is refluxed for 4 hours, cooled to RT and stirred with an ice/water mixture for 45 minutes. The reaction mixture is separated, extracted with methylene chloride and the combined extracts are washed with H2O, 5% aq. bicarbonate, H2O, dried, filtered and concentrated in vacuo, yielding a viscous oil, which is crystallized from ethyl acetate affording the desired product, M.P.=86°-88° C.

Workup

  1. customThe stirred reaction mixture
  2. temperatureis refluxed for 4 hours
  3. customThe reaction mixture is separated
  4. extractionextracted with methylene chloride
  5. washthe combined extracts are washed with H2O, 5% aq. bicarbonate, H2O
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customyielding a viscous oil, which
  10. customis crystallized from ethyl acetate affording the desired product, M.P.=86°-88° C.

Sources & evidence

ORD record
ord-ec67caa9cd1f4243a39652b5b1bc7408
Source dataset
uspto-grants-1989_04
Patent number
US04818755

Reaction notes

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