N-bromobutanimide → 6-bromo-7-fluoro-3,4-dihydroquinolin-2(1H)-one

HRID 1521638Notes

Reaction equation

HRID 1521638 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1.[Br:13]N1C(=O)CCC1=O>CN(C)C=O>[Br:13][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[F:1])[NH:9][C:8](=[O:12])[CH2:7][CH2:6]2

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 138300Carbostyril, 3,4-dihydro-7-fluoro-

Product 1

HCID 434576896-bromo-7-fluoro-3,4-dihydroquinolin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 7-fluoro-3,4-dihydroquinolin-2(1H)-one (122-2; 15 g, 0.090 mol) in N,N-dimethylformamide (50 mL) was added N-bromosuccinimide (19.22 g, 0.108 mol) portion wise at 0° C. Reaction mixture was allowed to stir at room temperature for 12 h. The reaction mixture was concentrated and diluted with ice cold water (150 mL) with constant stirring and the solid residue was filtered and dried to obtain the title compound. 1H NMR (400 MHz, CDCl3) δ 8.0 (bs, 1H), 7.34-7.32 (d, J=7.2 Hz, 1H), 6.59-6.57 (d, J=8.8 Hz, 1H), 2.95-2.91 (t, J=7.6 Hz, 2H), 2.65-2.61 (t, J=−7.6 Hz, 2H). MS (M+1): 245.9.

Workup

  1. customReaction mixture
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with ice cold water (150 mL)
  4. stirringwith constant stirring
  5. filtrationthe solid residue was filtered
  6. customdried

Sources & evidence

ORD record
ord-cdb67b7abcec4719baa5742932439951
Source dataset
uspto-grants-2015_07
Patent number
US09073929B2

Reaction notes

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