Water → HCID 59620340, compound

HRID 2070146Notes

Reaction equation

HRID 2070146 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([N+:12]([O-])=O)[CH:11]=1)[NH:8][C:7](=[O:15])[CH:6]([NH:16][C:17](=[O:19])[CH3:18])[CH2:5]2.C([O-])=O.[NH4+].O>C(O)C.[Pd]>[NH2:12][C:10]1[CH:11]=[CH:2][CH:3]=[C:4]2[C:9]=1[NH:8][C:7](=[O:15])[CH:6]([NH:16][C:17](=[O:19])[CH3:18])[CH2:5]2

Participants

6

Reactant 3

HCID 962WaterHCID 2723923Ammonium formateHCID 59620398HCID 59620398, compound

Product 1

HCID 59620340HCID 59620340, compoundYield 84.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Conditions

Temperature
80 °C

Procedure

N-(6-Bromo-8-nitro-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)acetamide (15 g) was suspended in ethanol (150 mL), and ammonium formate (28.8 g) and 10% Pd—C (water content: 53%) (1.5 g) were added thereto. The mixture was heated at 80° C. while being stirred for 30 minutes, and water (150 mL) and ethanol (150 mL) were added thereto, followed by filtration while being heated. The filtrate was concentrated under reduced pressure, and the formed precipitates were recovered through filtration. The thus-obtained solid was washed with ethanol and diisopropyl ether, followed by drying, whereby the title compound (8.5 g) was yielded.

Workup

  1. filtrationfollowed by filtration
  2. temperaturewhile being heated
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe formed precipitates
  5. filtrationwere recovered through filtration
  6. washThe thus-obtained solid was washed with ethanol and diisopropyl ether
  7. customby drying

Sources & evidence

ORD record
ord-058ec640b9c144c283f449fb6605c12c
Source dataset
uspto-grants-2012_10
Patent number
US08299255B2

Reaction notes

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