HCID 67492909, compound → HCID 67492764, compound

HRID 1922392Notes

Reaction equation

HRID 1922392 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([N+:18]([O-])=O)=[CH:15][CH:16]=3)[CH2:11][CH2:10][C:9]2=[O:21])[CH2:4][CH2:3]1.[H][H]>[Pd].C(O)C>[NH2:18][C:14]1[CH:13]=[C:12]2[C:17](=[CH:16][CH:15]=1)[N:8]([CH:5]1[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]1)[C:9](=[O:21])[CH2:10][CH2:11]2

Participants

5

Reactant 2

HCID 67492909HCID 67492909, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67492764HCID 67492764, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 1-(1-methylpiperidin-4-yl)-6-nitro-3,4-dihydroquinolin-2(1H)-one (300 mg, 1.04 mmol) and palladium on activated carbon (10% wt, 55 mg, 0.05 mmol) in 20 mL ethanol/4 mL THF was stirred under a balloon of hydrogen overnight. The suspension was filtered through a pad of celite. The filter pad was rinsed with 50 mL methanol, and the filtrate was concentrated to give a viscous oil. The crude product was used without further purification. (250 mg, 92.6%). 1H-NMR (CDCl3) δ 7.06 (d, J=9.3 Hz, 1H), 6.54-6.49 (m, 2H), 4.46-4.36 (m, 1H), 3.42 (brs, 2H), 2.97-2.94 (m, 2H), 2.73-2.49 (m, 6H), 2.31 (s, 3H), 2.27-2.05 (m, 2H), 1.27-1.21 (m, 2H). MS (ESI): 260.2 (M+1, 100%).

Workup

  1. filtrationThe suspension was filtered through a pad of celite
  2. washThe filter pad was rinsed with 50 mL methanol
  3. concentrationthe filtrate was concentrated
  4. customto give a viscous oil
  5. customThe crude product was used without further purification

Sources & evidence

ORD record
ord-8a82c893e2604bf89f607fb381786815
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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