Pyridine → tert-butyl 1-benzyl-8-(N-ethylacetamido)-2-oxo-1,2,3,4-tetrahydroquinolin-3-ylcarbamate

HRID 1887726Notes

Reaction equation

HRID 1887726 reaction equation
[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][C:16]=2[NH:18][CH2:19][CH3:20])[CH2:11][CH:10]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[C:9]1=[O:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1[CH:35]=[CH:34]C=CC=1.C(Cl)(=[O:38])C>ClCCCl>[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][C:16]=2[N:18]([CH2:34][CH3:35])[C:19](=[O:38])[CH3:20])[CH2:11][CH:10]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:25])([CH3:27])[CH3:26])[C:9]1=[O:29])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 59620343Tert-butyl 1-benzyl-8-ethylamino-1,2,3,4-tetrahydro-2-oxoquinolin-3-ylcarbamate

Product 1

HCID 59620393tert-butyl 1-benzyl-8-(N-ethylacetamido)-2-oxo-1,2,3,4-tetrahydroquinolin-3-ylcarbamate

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

tert-Butyl 1-benzyl-8-ethylamino-1,2,3,4-tetrahydro-2-oxoquinolin-3-ylcarbamate (300 mg) was dissolved in 1,2-dichloroethane (2.5 mL), and pyridine (180 mg) was added to the solution. Under cooling on ice, a solution of acetyl chloride (179 mg) in 1,2-dichloroethane (2.5 mL) was added dropwise to the mixture. The resultant mixture was stirred at room temperature for two hours, and the reaction mixture was concentrated under reduced pressure. Water was added to the thus-recovered residue, and the mixture was subjected to extraction with ethyl acetate. The organic layer was sequentially washed with 0.1N HCl, saturated aqueous sodium bicarbonate solution, and saturated aqueous sodium chloride solution, and dried over sodium sulfate. Solvent was evaporated under reduced pressure, whereby the title compound (330 mg) was yielded.

Workup

  1. temperatureUnder cooling on ice
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. additionWater was added to the thus-recovered residue
  4. extractionthe mixture was subjected to extraction with ethyl acetate
  5. washThe organic layer was sequentially washed with 0.1N HCl, saturated aqueous sodium bicarbonate solution, and saturated aqueous sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. customSolvent was evaporated under reduced pressure, whereby the title compound (330 mg)
  8. customwas yielded

Sources & evidence

ORD record
ord-c18bd312ccf841dbb908636aa0ca414d
Source dataset
uspto-grants-2013_08
Patent number
US08501772B2

Reaction notes

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