Hydrazine hydrate (1:1) → 6-amino-1-(2-(pyrrolidin-1-yl)ethyl)-3,4-dihydroquinolin-2(1H)-one

HRID 1922349Notes

Reaction equation

HRID 1922349 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[CH2:20][CH2:19][CH2:18][CH2:17]1)[C:9](=[O:21])[CH2:8][CH2:7]2)([O-])=O.O.NN>CO.[Ni]>[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]1)[C:9](=[O:21])[CH2:8][CH2:7]2

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 53392094HCID 53392094, compound

Product 1

HCID 533921826-amino-1-(2-(pyrrolidin-1-yl)ethyl)-3,4-dihydroquinolin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To solution of 6-nitro-1-(2-(pyrrolidin-1-yl)ethyl)-3,4-dihydroquinolin-2(1H)-one (205 mg, 0.709 mmol) in 5 mL methanol was added to Raney Nickel (slurry in H2O, 50 mg) in a reaction vial. The suspension was treated with hydrazine hydrate (220 μL, 7.09 mmol) and heated at reflux for 2 hours and then filtered through a pad of celite. The celite pad was rinsed with 10 mL methanol. The filtrate was concentrated and the resulting product was subjected to flash silica gel chromatography using 2.5% 2M NH3 in MeOH/CH2Cl2 to afford a yellow oil. Yield: 180 mg (98%). 1H NMR (CDCl3) δ: 6.89 (d, J=8.4 Hz, 1H), 6.56 (dd, J=2.7, 8.4 Hz, 1H), 6.52 (d, J=2.1 Hz, 1H), 4.04 (t, J=7.5 Hz, 2H), 2.81-2.76 (m, 2H), 2.71-2.66 (m, 2H), 2.63-2.56 (m, 6H), 1.81-1.77 (m, 4H). MS (ESI): 260.2 (M+1, 100%).

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hours
  3. filtrationfiltered through a pad of celite
  4. washThe celite pad was rinsed with 10 mL methanol
  5. concentrationThe filtrate was concentrated
  6. customto afford a yellow oil

Sources & evidence

ORD record
ord-248b3404b4c24de98d9f8341debff7fb
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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