HCID 53392179, compound → HCID 53392183, compound

HRID 1922373Notes

Reaction equation

HRID 1922373 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[CH2:7][CH2:8][N:9]1[C:18]2[C:13](=[CH:14][C:15]([N+:19]([O-])=O)=[CH:16][CH:17]=2)[CH2:12][CH2:11][C:10]1=[O:22].[H][H]>[Pd].C(O)C.CO.C(Cl)Cl>[NH2:19][C:15]1[CH:14]=[C:13]2[C:18](=[CH:17][CH:16]=1)[N:9]([CH2:8][CH2:7][CH:3]1[CH2:4][CH2:5][CH2:6][N:2]1[CH3:1])[C:10](=[O:22])[CH2:11][CH2:12]2

Participants

6

Reactant 2

HCID 53392179HCID 53392179, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53392183HCID 53392183, compoundYield 73%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

A suspension of 1-(2-(1-methylpyrrolidin-2-yl)ethyl)-6-nitro-3,4-dihydroquinolin-2(1H)-one (2.25 g, 7.42 mmol) and palladium on activated carbon (10%, 100 mg, 0.09 mmol) in 50 mL ethanol was stirred under a balloon of hydrogen for 2 days. The suspension was filtered through a pad of celite. The filter pad was rinsed with 50 mL ethanol and the filtrate was concentrated to give a viscous oil. The crude product was subjected to Biotage flash chromatography on silica gel using 0-5% 2M NH3 in MeOH/CH2Cl2 to give a yellow foam (1.48 g, 72.9%). 1H-NMR (CDCl3) δ: 6.82 (d, J=8.4 Hz, 1H), 6.55 (dd, J=3.0, 8.4 Hz, 1H), 6.52 (d, J=3.0 Hz, 1H), 4.09-3.99 (m, 1H), 3.86-3.76 (m, 1H), 3.54 (br s, 2H), 3.04-3.01 (m, 1H), 2.81-2.76 (m, 2H), 2.61-2.56 (m, 2H), 2.29 (s, 3H), 2.17-1.60 (m, 8H).

Workup

  1. filtrationThe suspension was filtered through a pad of celite
  2. washThe filter pad was rinsed with 50 mL ethanol
  3. concentrationthe filtrate was concentrated
  4. customto give a viscous oil

Sources & evidence

ORD record
ord-1fffc9d653624509927312d0a95f9a4f
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

Loading…