1,1-Dichloroethane → HCID 67506105, compound

HRID 2105472Notes

Reaction equation

HRID 2105472 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[Cl:12])=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH3:13][C:14]([CH3:19])([CH3:18])[C:15](Cl)=[O:16].ClC(Cl)C>ClCCl>[Cl:12][C:11]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[CH:3][C:2]=1[NH:1][C:15](=[O:16])[C:14]([CH3:19])([CH3:18])[CH3:13]

Participants

5

Reactant 3

HCID 63651,1-DichloroethaneHCID 62493Pivaloyl chloride2×HCID 8173324-chloroquinolin-3-amine

Product 1

HCID 67506105HCID 67506105, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3-amino-4-chloroquinoline (8.00 g, 1 eq), trimethylacetyl chloride (11 mL g, 2 eq), and anhydrous dichloroethane (150 mL) was heated at 70° C. After 6 hours more trimethylacetyl chloride (2 eq) was added and heating was continued for a total of 23 hours. The reaction mixture was diluted with dichloromethane, washed sequentially with saturated aqueous potassium carbonate, water, and brine, dried over sodium sulfate, filtered, and then concentrated under reduced pressure. The residue was triturated with hexanes and then filtered to provide 7.16 g of N-(4-chloroquinolin-3-yl)trimethylacetamide as a solid. The filtrate was concentrated under reduced pressure to provide 5 g of crude N-(4-chloroquinolin-3-yl)trimethylacetamide.

Workup

  1. temperatureheating
  2. customwas continued for a total of 23 hours
  3. washwashed sequentially with saturated aqueous potassium carbonate, water, and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was triturated with hexanes
  8. filtrationfiltered

Sources & evidence

ORD record
ord-fd32fdf9a6d54bb79088cf444f83c055
Source dataset
uspto-grants-2009_08
Patent number
US07579359B2

Reaction notes

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