Ammonia → HCID 53392181, compound

HRID 1922336Notes

Reaction equation

HRID 1922336 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)[C:9](=[O:22])[CH2:8][CH2:7]2)([O-])=O.N>CO.[Ni].CO.C(Cl)Cl>[NH2:1][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH2:14][CH2:15][N:16]1[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1)[C:9](=[O:22])[CH2:8][CH2:7]2

Participants

6

Reactant 2

HCID 222AmmoniaHCID 53392093HCID 53392093, compound

Product 1

HCID 53392181HCID 53392181, compoundYield 77.7%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

A solution of 6-nitro-1-(2-(piperidin-1-yl)ethyl)-3,4-dihydroquinolin-2(1H)-one (500 mg, 1.65 mmol) in 10 mL methanol was added to Raney Nickel (slurry in H2O, 50 mg) in a round bottom flask. The suspension was heated at reflux for 10 minutes then filtered through a pad of celite. The celite pad was washed with 10 mL methanol. The filtrate was concentrated to give a dark brown residue was subjected to flash silica gel chromatography using 5% 2M NH3 in MeOH/CH2Cl2 to give an off-white solid (350 mg, 77.7%). 1H-NMR (DMSO-d6) δ: 6.81 (d, J=8.2 Hz, 1H), 6.46-6.41 (m, 2H), 4.84 (br s, 2H), 3.87 (t, J=7.1 Hz, 2H), 2.66 (t, J=6.5 Hz, 2H), 2.40-2.32 (m, 8H), 1.46-1.35 (m, 6H); MS (ESI): 274.2 (M+1, 100%).

Workup

  1. temperatureThe suspension was heated
  2. temperatureat reflux for 10 minutes
  3. filtrationthen filtered through a pad of celite
  4. washThe celite pad was washed with 10 mL methanol
  5. concentrationThe filtrate was concentrated
  6. customto give a dark brown residue

Sources & evidence

ORD record
ord-f844cb444ef64975a4120888f389d74c
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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