Bromoacetyl chloride → HCID 14032992, compound

HRID 620014Notes

Reaction equation

HRID 620014 reaction equation
[Br:1][CH2:2][C:3](Cl)=[O:4].[CH3:6][N:7]1[C:16]2[CH:11]([CH2:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9][C:8]1=[O:17].[Al+3].[Cl-].[Cl-].[Cl-]>C(Cl)Cl>[Br:1][CH2:2][C:3]([C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[N:7]([CH3:6])[C:8](=[O:17])[CH2:9][CH2:10]2)=[O:4]

Participants

5

Reactant 3

HCID 89602Bromoacetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 70054036HCID 70054036, compound

Product 1

HCID 14032992HCID 14032992, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Bromoacetyl chloride (28.3 g) is added dropwise to a suspension of N-methyl-tetrahydroquinolin-2-one (14.7 g) and AlCl3 (26.7 g) in methylene chloride (400 ml), and the reaction mixture is refluxed for 5 hours. The reaction mixture is cooled to RT, stirred with an ice/water mixture for 30 minutes, diluted with methylene chloride (200 ml) and separated. The aqueous layer is extracted with methylene chloride, and the combined organic extracts are washed with H2O, dried, filtered and concentrated in vacuo, yielding a crude solid which is recrystallized from isopropanol affording the desired product as a solid.

Workup

  1. temperaturethe reaction mixture is refluxed for 5 hours
  2. customseparated
  3. extractionThe aqueous layer is extracted with methylene chloride
  4. washthe combined organic extracts are washed with H2O
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customyielding a crude solid which
  9. customis recrystallized from isopropanol affording the desired product as a solid

Sources & evidence

ORD record
ord-f66d923ad19540698fc541ed04eb1bef
Source dataset
uspto-grants-1989_04
Patent number
US04818755

Reaction notes

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