Acetic Acid → HCID 22266484, compound

HRID 489295Notes

Reaction equation

HRID 489295 reaction equation
C(OC(=O)[NH:10][C:11]1[C:12](=[O:25])[N:13]([CH2:21][CH2:22][CH2:23][CH3:24])[C:14]2[CH2:15][CH2:16][CH2:17][CH2:18][C:19]=2[CH:20]=1)C1C=CC=CC=1.[C:27]([OH:30])(=[O:29])[CH3:28]>CO.[Pd]>[C:27]([OH:30])(=[O:29])[CH3:28].[NH2:10][C:11]1[C:12](=[O:25])[N:13]([CH2:21][CH2:22][CH2:23][CH3:24])[C:14]2[CH2:15][CH2:16][CH2:17][CH2:18][C:19]=2[CH:20]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 23587938HCID 23587938, compound

Product 1

HCID 22266484HCID 22266484, compoundYield 76.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(1-Butyl-2-oxo-1,2,5,6,7,8-hexahydroquinolin-3-yl)carbamic acid benzyl ester (6-007) (100 mg, 0.28 mmol) was dissolved in methanol (7 mL), and to the reaction mixture were added acetic acid (16 μL, 0.28 mmol) and palladium on carbon (10%, 30 mg), and the reaction mixture was stirred vigorously under hydrogen atmosphere for 1.5 h. Palladium on carbon was filtered off, and the filtrate was concentrated under reduced pressure, and the crystalloid residue was recrystallized from hexane to give 3-amino-1-butyl-5,6,7,8-tetrahydro-1H-quinolin-2-one acetic acid salt (6-001-01) (60 mg, 76%) as a white crystal.

Workup

  1. filtrationPalladium on carbon was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customthe crystalloid residue was recrystallized from hexane

Sources & evidence

ORD record
ord-dc45c32f28df4c8ab4e810fc4f7ee07a
Source dataset
uspto-grants-2005_12
Patent number
US06977266B2

Reaction notes

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