Ethyl Acetate → HCID 21894663, compound

HRID 1242916Notes

Reaction equation

HRID 1242916 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[CH2:8][CH2:9][CH2:10][CH2:11][C:12]=2[CH:13]=1)([O-])=O.[C:14](OCC)(=[O:16])[CH3:15]>[C].[Pd].CO>[N:6]1[C:7]2[CH2:8][CH2:9][CH2:10][CH2:11][C:12]=2[CH:13]=[C:4]([NH:1][C:14](=[O:16])[CH3:15])[CH:5]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 110303733-nitro-5,6,7,8-tetrahydroquinoline

Product 1

HCID 21894663HCID 21894663, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

10% Palladium-carbon (200 mg) was added to a methanol solution (68 ml) of 3-nitro-5,6,7,8-tetrahydroquinoline (2.41 g], 13.5 mmol) obtained in 2), which was stirred under hydrogen atmosphere for 16 hours. After a catalyst was filtered off, the solvent was distilled out under reduced pressure. The resulting residue was dissolved in pyridine (35 ml). Anhydrous ethyl acetate (1.91 ml, 20.3 mmol) was added to the solution, which was stirred at room temperature for 1 hour. After completion of the reaction, the solvent was distilled out under reduced pressure. Diisopropyl ether-n-hexane (1:8) was added to the resulting residue, to give the titled compound (2.48 g) as a colorless powder.

Workup

  1. customobtained in 2), which
  2. filtrationAfter a catalyst was filtered off
  3. distillationthe solvent was distilled out under reduced pressure
  4. dissolutionThe resulting residue was dissolved in pyridine (35 ml)
  5. stirringwas stirred at room temperature for 1 hour
  6. customAfter completion of the reaction
  7. distillationthe solvent was distilled out under reduced pressure
  8. additionDiisopropyl ether-n-hexane (1:8) was added to the resulting residue

Sources & evidence

ORD record
ord-d2530d02b18e46409dac244a5ac42687
Source dataset
uspto-grants-2006_10
Patent number
US07115750B1

Reaction notes

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