Triethylamine → HCID 57447055, compound

HRID 2366662Notes

Reaction equation

HRID 2366662 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].C(N(CC)CC)C.[NH2:22][CH2:23][C:24]([CH3:31])([CH3:30])[C:25]([O:27][CH2:28][CH3:29])=[O:26].C(=O)([O-])[O-].[K+].[K+].C(=O)(O)[O-].[Na+]>ClCCl>[CH3:30][C:24]([CH3:31])([CH2:23][NH:22][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13])[C:25]([O:27][CH2:28][CH3:29])=[O:26]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 421529Ethyl 3-amino-2,2-dimethylpropanoate3×HCID 516892Sodium BicarbonateHCID 112758084-Chloro-3-nitroquinoline

Product 1

HCID 57447055HCID 57447055, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A suspension of 4-chloro-3-nitroquinoline (35.0 g, 168 mmol) and triethylamine (84 mL, 0.60 mol) in dichloromethane (400 mL) was cooled to 0° C.; a solution of ethyl 3-amino-2,2-dimethylpropanoate (40.0 g, 0.220 mol) in dichloromethane (50 mL) was added dropwise. The reaction was stirred at 0° C. for 30 minutes and then at ambient temperature for four hours. The reaction was incomplete as determined by a TLC analysis, and additional ethyl 3-amino-2,2-dimethylpropionate (10.0 g, 55.0 mmol) was added. The reaction was stirred overnight; another analysis by TLC indicated the reaction was incomplete. Additional ethyl 3-amino-2,2-dimethylpropionate (5.0 g, 28 mmol) was added, and the reaction was heated at reflux for three hours. Potassium carbonate (10 g) was added, and the reaction was heated at reflux for two hours and stirred overnight at ambient temperature. Saturated aqueous sodium bicarbonate (50 mL) was added, and the reaction was stirred for three days. The organic layer was separated, washed with water (3×100 mL), dried over potassium carbonate, filtered, and concentrated under reduced pressure to provide ethyl 2,2-dimethyl-3-[(3-nitroquinolin-4-yl)amino]propanoate as an orange oil, which was mixed with material from another run and used without purification.

Workup

  1. waitat ambient temperature for four hours
  2. additionwas added
  3. stirringThe reaction was stirred overnight
  4. temperaturethe reaction was heated
  5. temperatureat reflux for three hours
  6. temperaturethe reaction was heated
  7. temperatureat reflux for two hours
  8. stirringstirred overnight at ambient temperature
  9. stirringthe reaction was stirred for three days
  10. customThe organic layer was separated
  11. washwashed with water (3×100 mL)
  12. dry with materialdried over potassium carbonate
  13. filtrationfiltered
  14. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cccdc1e782c24c4788efaea90bf2295a
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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