N-bromobutanimide → 6-bromo-5-cyclopropyl-3,4-dihydroquinolin-2(1H)-one

HRID 1521665Notes

Reaction equation

HRID 1521665 reaction equation
[CH:1]1([C:4]2[CH:13]=[CH:12][CH:11]=[C:10]3[C:5]=2[CH2:6][CH2:7][C:8](=[O:14])[NH:9]3)[CH2:3][CH2:2]1.[Br:15]N1C(=O)CCC1=O>CN(C)C=O>[Br:15][C:13]1[C:4]([CH:1]2[CH2:3][CH2:2]2)=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:14])[CH2:7][CH2:6]2

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 891570455-cyclopropyl-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 709791496-bromo-5-cyclopropyl-3,4-dihydroquinolin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 5-cyclopropyl-3,4-dihydroquinolin-2(1H)-one (147-5; 0.5 g, 0.00267 mol) in N,N-dimethylformamide (10 mL) was added N-bromosuccinimide (0.47 g, 0.0026 mol) portion wise at 0° C. Reaction mixture was allowed to stir at room temperature for 4 h. The reaction mixture was concentrated and diluted with ice cold water (100 mL) with constant stirring, the solid residue obtained was filtered and dried to obtain the title compound. MS (M+1): 266.1.

Workup

  1. customReaction mixture
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with ice cold water (100 mL) with constant stirring
  4. customthe solid residue obtained
  5. filtrationwas filtered
  6. customdried

Sources & evidence

ORD record
ord-9db4c85d43d6475e8515f7be83bbcdf5
Source dataset
uspto-grants-2015_07
Patent number
US09073929B2

Reaction notes

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