Ammonia → HCID 43446597, compound

HRID 1922339Notes

Reaction equation

HRID 1922339 reaction equation
[CH2:1]([N:3]([CH2:20][CH3:21])[CH2:4][CH2:5][N:6]1[C:15]2[C:10](=[CH:11][C:12]([N+:16]([O-])=O)=[CH:13][CH:14]=2)[CH2:9][CH2:8][C:7]1=[O:19])[CH3:2].O.NN.N>CO.[Ni].CO.C(Cl)Cl>[NH2:16][C:12]1[CH:11]=[C:10]2[C:15](=[CH:14][CH:13]=1)[N:6]([CH2:5][CH2:4][N:3]([CH2:20][CH3:21])[CH2:1][CH3:2])[C:7](=[O:19])[CH2:8][CH2:9]2

Participants

7

Reactant 3

HCID 222AmmoniaHCID 24654Hydrazine hydrate (1:1)HCID 53392092HCID 53392092, compound

Product 1

HCID 43446597HCID 43446597, compoundYield 81.2%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

A solution of 1-(2-(diethylamino)ethyl)-6-nitro-3,4-dihydroquinolin-2(1H)-one (500 mg, 1.72 mmol) in 10 mL methanol was added to Raney Nickel (slurry in H2O, 50 mg) in a round bottom flask. The suspension was treated with hydrazine hydrate (534 μL, 17.2 mmol) and heated at reflux for 10 minutes then filtered through a pad of celite. The celite pad was rinsed with 10 mL methanol. The filtrate was concentrated to give a dark brown residue which was subjected to flash silica gel chromatography using 5% 2M NH3 in MeOH/CH2Cl2 to give a colorless oil (365 mg, 81.2%). 1H-NMR (CDCl3) δ: 6.88 (d, J=8.4 Hz, 1H), 6.58 (d, J=2.7 Hz, 1H), 6.51 (dd, J=2.7, 9 Hz, 1H), 3.98 (t, J=7.8 Hz, 2H), 3.54 (br s, 2H), 2.78 (t, J=7.8 Hz, 2H), 2.66-2.55 (m, 8H), 1.04 (t, J=7.2 Hz, 6H). MS (ESI): 262.2 (M+1, 100%).

Workup

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

Sources & evidence

ORD record
ord-19e5c95641974e788da572a4259789de
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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