Ammonia → 6-amino-3-(3-(dimethylamino)propyl)-1-(4-methoxybenzyl)-3,4-dihydroquinolin-2(1H)-one

HRID 1922362Notes

Reaction equation

HRID 1922362 reaction equation
[CH3:1][N:2]([CH3:29])[CH2:3][CH2:4][CH2:5][CH:6]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([N+:16]([O-])=O)[CH:13]=2)[N:8]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[C:7]1=[O:28].O.NN.N>CO.[Ni].CO.C(Cl)Cl>[NH2:16][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)[C:7](=[O:28])[CH:6]([CH2:5][CH2:4][CH2:3][N:2]([CH3:29])[CH3:1])[CH2:15]2

Participants

7

Reactant 3

HCID 222AmmoniaHCID 24654Hydrazine hydrate (1:1)HCID 598071213-(3-(dimethylamino)propyl)-1-(4-methoxybenzyl)-6-nitro-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 598071226-amino-3-(3-(dimethylamino)propyl)-1-(4-methoxybenzyl)-3,4-dihydroquinolin-2(1H)-oneYield 72.3%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

A solution of 3-(3-(dimethylamino)propyl)-1-(4-methoxybenzyl)-6-nitro-3,4-dihydroquinolin-2(1H)-one (115 mg, 0.29 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 (90 μL, 2.90 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 yellow residue which was subjected to flash silica gel chromatography using 5% 2M NH3 in MeOH/CH2Cl2 to give a yellow semi-solid (77 mg, 72.3%). 1H-NMR (CDCl3) δ: 7.13-7.10 (m, 2H), 6.83-6.80 (m, 2H), 6.69 (d, J=8.4 Hz, 1H), 6.50 (d, J=2.4 Hz, 1H), 6.42 (dd, J=2.4, 8.4 Hz, 1H), 5.05 (dd, J=15.6, 29.1 Hz, 2H), 3.76 (s, 3H), 3.48 (br s, 2H), 3.01-2.91 (m, 1H), 2.70-2.58 (m, 2H), 2.28 (t, J=7.2 Hz, 2H), 2.21 (s, 6H), 1.88-1.42 (m, 4H).

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 yellow residue which

Sources & evidence

ORD record
ord-e5ed9ab17a594e17a7c2c11fd005049b
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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