Dimethylamine → HCID 22282638, compound

HRID 1583058Notes

Reaction equation

HRID 1583058 reaction equation
Br[C:2]1[CH:11]=[C:10]([Br:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:13][NH:14][CH3:15]>O>[Br:12][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]([N:14]([CH3:15])[CH3:13])[CH:11]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 8246082,4-dibromoquinoline

Product 1

HCID 22282638HCID 22282638, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

The product from (451a) (2.0 g, 7.0 mmol) was dissolved in 10 mL of 40% dimethylamine solution in H2O. The reaction mixture was allowed to stir overnight. The solution was diluted to 40 mL with H2O and it was extracted with EtOAc for three times. The combined organic layer was dried over MgSO4. After concentration, the residue was purified on silica gel column to provide 4-bromo-2-dimethylaminoquinoline (451b) (0.69 g, 40%). MS (AP+): 251 (M+1).

Workup

  1. extractionwas extracted with EtOAc for three times
  2. dry with materialThe combined organic layer was dried over MgSO4
  3. concentrationAfter concentration
  4. customthe residue was purified on silica gel column

Sources & evidence

ORD record
ord-d953b726c1114df48f7b3dd114e2fb1d
Source dataset
uspto-grants-2004_05
Patent number
US06740649B2

Reaction notes

Loading…