HCID 66812993, compound → HCID 59322835, compound

HRID 1669687Notes

Reaction equation

HRID 1669687 reaction equation
[O:1]=[C:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2/[CH:12]=[CH:13]/[C:14]([O:16]CC)=[O:15])[NH:3]1>CO.[Pd]>[O:1]=[C:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[CH2:12][CH2:13][C:14]([OH:16])=[O:15])[NH:3]1

Participants

4

Reactant 1

HCID 66812993HCID 66812993, compound

Product 1

HCID 59322835HCID 59322835, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 10% Pd/C (5 mg) and ethyl (2E)-3-(2-oxo-1,2,3,4-tetrahydroquinolin-5-yl)acrylate from Step B (16 mg, 0.065 mmol) was stirred vigorously in MeOH (2 mL) under an atmosphere of hydrogen (ca. 1 atm). After 4 h, the mixture was filtered through a pad of Celite, washing with MeOH, and the filtrate was concentrated. The residue was dissolved in MeOH (1 mL) and 1 N aqueous NaOH (0.1 mL) and the resulting mixture was stirred at ambient temperature for 18 h. To the reaction mixture was added 1 N aqueous HCl (0.1 mL) and the resulting mixture was concentrated to dryness under reduced pressure to give the title compound. MS: m/z=220 (M+1).

Workup

  1. filtrationthe mixture was filtered through a pad of Celite
  2. washwashing with MeOH
  3. concentrationthe filtrate was concentrated
  4. dissolutionThe residue was dissolved in MeOH (1 mL)
  5. additionTo the reaction mixture was added 1 N aqueous HCl (0.1 mL)
  6. concentrationthe resulting mixture was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-fd53d5f672a3479abcb31a22b38710e5
Source dataset
uspto-grants-2011_08
Patent number
US07989624B2

Reaction notes

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