N-bromobutanimide → 6-Bromo-2-oxo-1,2,3,4-tetrahydroquinoline-5-carbonitrile

HRID 1521651Notes

Reaction equation

HRID 1521651 reaction equation
[O:1]=[C:2]1[CH2:11][CH2:10][C:9]2[C:8]([C:12]#[N:13])=[CH:7][CH:6]=[CH:5][C:4]=2[NH:3]1.[Br:14]N1C(=O)CCC1=O>CN(C)C=O>[Br:14][C:7]1[CH:6]=[CH:5][C:4]2[NH:3][C:2](=[O:1])[CH2:11][CH2:10][C:9]=2[C:8]=1[C:12]#[N:13]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 665969262-Oxo-1,2,3,4-tetrahydroquinoline-5-carbonitrile

Product 1

HCID 709774556-Bromo-2-oxo-1,2,3,4-tetrahydroquinoline-5-carbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2-oxo-1,2,3,4-tetrahydroquinoline-5-carbonitrile (145-1; 1.5 g, 0.0087 mol) in N,N-dimethylformamide (10 mL) was added N-bromosuccinimide (1.8 g, 0.01046 mol) portion wise at 0° C. Reaction mixture was allowed to stir at room temperature for 12 h. It 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): 251.2.

Workup

  1. customReaction mixture
  2. concentrationIt 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-d5c8284b8c6047dc81e845e1645b92ae
Source dataset
uspto-grants-2015_07
Patent number
US09073929B2

Reaction notes

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