Dimethylformamide → 6-bromo-N,N-dimethylquinoline-2-carboxamide

HRID 2167496Notes

Reaction equation

HRID 2167496 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]([OH:14])=O)[CH:6]=[CH:5]2.[CH3:15][N:16](C=O)[CH3:17].C(Cl)(=O)C(Cl)=O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]([N:16]([CH3:17])[CH3:15])=[O:14])[CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 123862086-Bromoquinoline-2-carboxylic acid

Product 1

HCID 581193586-bromo-N,N-dimethylquinoline-2-carboxamideYield 90.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Suspended the 6-bromoquinoline-2-carboxylic acid (1.0 g, 3.93 mmol) in CH2Cl2 (20 mL), added DMF (0.91 mL, 11.78 mmol) and cooled in an ice bath. Added oxalyl chloride (0.688 mL, 7.86 mmol) dropwise over a few min. Warmed to rt and stirred for 1 hr then bubbled in dimethylamine gas for several min. The dark amber mixture was stirred at rt overnight. In am, the solution was diluted with water and extracted with CH2Cl2 (3×). Washed extracts with brine (1×), dried over MgSO4, decolorized with charcoal, filtered, evaporated and dried under high vac, rt to afford the title compound (990 mg). LC/MS: m/e 279, 281 (M+H)+.

Workup

  1. temperaturecooled in an ice bath
  2. customthen bubbled in dimethylamine gas for several min
  3. stirringThe dark amber mixture was stirred at rt overnight
  4. additionthe solution was diluted with water
  5. extractionextracted with CH2Cl2 (3×)
  6. dry with materialWashed extracts with brine (1×), dried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customdried under high vac, rt

Sources & evidence

ORD record
ord-d736c133fcd14cfa8aa9f28f7703a3b9
Source dataset
uspto-grants-2015_06
Patent number
US09045467B2

Reaction notes

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