Hydrazine hydrate (1:1) → HCID 43446585, compound

HRID 1922341Notes

Reaction equation

HRID 1922341 reaction equation
[CH3:1][N:2]([CH3:19])[CH2:3][CH2:4][N:5]1[C:14]2[C:9](=[CH:10][C:11]([N+:15]([O-])=O)=[CH:12][CH:13]=2)[CH2:8][CH2:7][C:6]1=[O:18].O.NN>CO.[Ni]>[NH2:15][C:11]1[CH:10]=[C:9]2[C:14](=[CH:13][CH:12]=1)[N:5]([CH2:4][CH2:3][N:2]([CH3:1])[CH3:19])[C:6](=[O:18])[CH2:7][CH2:8]2

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 533920911-(2-(dimethylamino)ethyl)-6-nitro-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 43446585HCID 43446585, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A suspension of 1-(2-(dimethylamino)ethyl)-6-nitro-3,4-dihydroquinolin-2(1H)-one (320 mg, 1.215 mmol) in dry methanol (10 mL) was treated with Ra—Ni (˜0.05 g) followed by hydrazine hydrate (0.38 mL, 12.2 mmol) at room temperature and the resulting mixture was refluxed for 20 min. The colorless reaction was cooled to room temperature, filtered through a celite pad, washed with methanol (2×10 mL). The combined methanol layer was evaporated and crude was purified by column chromatography (2 M NH3 in MeOH:CH2Cl2, 5:95). Yield: 280 mg of colorless oil (98%). 1H NMR (CDCl3) δ: 6.86 (d, J=8.4 Hz, 1H), 6.57 (dd, J=2.7, 8.4 Hz, 1H), 6.51 (d, J=2.1 Hz, 1H), 4.01 (t, J=7.5 Hz, 2H), 2.78 (t, J=7.2 Hz, 2H), 2.58 (t, J=7.2 Hz, 2H), 2.51 (t, J=7.2 Hz, 2H), 2.31 (s, 6H). MS (ESI): 234.2 (M+1).

Workup

  1. temperaturethe resulting mixture was refluxed for 20 min
  2. customThe colorless reaction
  3. filtrationfiltered through a celite pad
  4. washwashed with methanol (2×10 mL)
  5. customThe combined methanol layer was evaporated
  6. customcrude was purified by column chromatography (2 M NH3 in MeOH:CH2Cl2, 5:95)

Sources & evidence

ORD record
ord-13b93475bf2e441ab616df8e58f51959
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

Loading…