1-Bromo-2-Chloroethane → [3-(2-Chloroethoxy)phenyl]-(2-methylquinolin-4-yl)amine

HRID 914970Notes

Reaction equation

HRID 914970 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([NH:12][C:13]2[CH:14]=[C:15]([OH:19])[CH:16]=[CH:17][CH:18]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.Br[CH2:21][CH2:22][Cl:23].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:23][CH2:22][CH2:21][O:19][C:15]1[CH:14]=[C:13]([NH:12][C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=[C:2]([CH3:1])[CH:11]=2)[CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 9426933-(2-Methylquinolin-4-ylamino)phenol

Product 1

HCID 58958224[3-(2-Chloroethoxy)phenyl]-(2-methylquinolin-4-yl)amineYield 44.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
70 °C

Procedure

To a heterogeneous mixture of 20 (2.16 g, 6.90 mmol) in acetone (22 mL) were sequentially added 1-bromo-2-chloroethane (7.2 mL, 86.50 mmol) and potassium carbonate (3.00 g, 21.71 mmol). The reaction was stirred and heated at 70° C. for 17 hours before it was allowed to cool to room temperature and was filtered. The solids were rinsed with a 3:1 mixture of dichloromethane/methanol (25 mL×3), and the filtrate was isolated and evaporated to give the crude product. Column chromatography on silica (dichloromethane to 20/1 to 15/1 to 5/1dichloromethane/methanol) gave 21 as a pale yellow solid (0.96 g, 35.5%).

Workup

  1. temperatureto cool to room temperature
  2. filtrationwas filtered
  3. washThe solids were rinsed with a 3:1 mixture of dichloromethane/methanol (25 mL×3)
  4. customthe filtrate was isolated
  5. customevaporated
  6. customto give the crude product

Sources & evidence

ORD record
ord-5ce5cf88236940699ceb6ad9166a02fa
Source dataset
uspto-grants-2007_09
Patent number
US07265122B2

Reaction notes

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