N-bromobutanimide → 6-Bromo-1,2,3,4-tetrahydroquinoline

HRID 1515333Notes

Reaction equation

HRID 1515333 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[Br:11]N1C(=O)CCC1=O>CN(C)C=O.O>[Br:11][C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[NH:1][CH2:2][CH2:3][CH2:4]2

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 694601,2,3,4-Tetrahydroquinoline

Product 1

HCID 47150296-Bromo-1,2,3,4-tetrahydroquinolineYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 1,2,3,4-tetrahydroquinoline (100 mg) in N,N-dimethylformamide (1 ml), a solution of N-bromosuccinimide (134 mg) in N,N-dimethylformamide (1 ml) was added dropwise under ice cooling and stirred at the same temperature for 1 hour. The reaction mixture was diluted with water and extracted with ethyl acetate. The extracted organic layer was washed sequentially with water and brine, dried over anhydrous magnesium sulfate and then filtered to remove the desiccant, followed by distilling off the solvent under reduced pressure to give 6-bromo-1,2,3,4-tetrahydroquinoline (137 mg) as a yellow oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extracted organic layer was washed sequentially with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customto remove the desiccant
  6. distillationby distilling off the solvent under reduced pressure

Sources & evidence

ORD record
ord-936ad1fff6184a30901136db014cbb35
Source dataset
uspto-grants-2012_07
Patent number
US08222417B2

Reaction notes

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