Hydrazine hydrate (1:1) → HCID 59807143, compound

HRID 1922357Notes

Reaction equation

HRID 1922357 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][CH2:16][N:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)[C:9](=[O:23])[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][CH2:16][N:17]1[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1)[C:9](=[O:23])[CH2:8][CH2:7]2

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 59807102HCID 59807102, compound

Product 1

HCID 59807143HCID 59807143, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

6-nitro-1-(3-(piperidin-1-yl)propyl)-3,4-dihydroquinolin-2(1H)-one (98 mg, 0.309 mmol) in dry methanol (5 mL) was treated with Ra—Ni (˜0.05 g slurry in water) followed by hydrazine hydrate (96 uL, 3.08 mmol) at room temperature and the resulting mixture was refluxed for 30 minutes. The reaction was cooled to room temperature, filtered through a celite bed, 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, 2.5:97.5). Yield: 71 mg of yellow oil (80%). 1H NMR (CDCl3) δ: 6.90 (d, J=8.4 Hz, 1H), 6.55 (dd, J=2.7, 8.4 Hz, 1H), 6.51 (d, J=2.1 Hz, 1H), 3.91 (m, 2H), 2.80-2.76 (m, 2H), 2.61-2.56 (m, 2H), 2.38-2.33 (m, 6H), 1.84-1.79 (m, 2H), 1.60-1.55 (m, 4H), 1.46-1.42 (m, 2H). MS (ESI): 288.2 (M+1).

Workup

  1. temperaturethe resulting mixture was refluxed for 30 minutes
  2. filtrationfiltered through a celite bed
  3. washwashed with methanol (2×10 mL)
  4. customThe combined methanol layer was evaporated
  5. customcrude was purified by column chromatography (2 M NH3 in MeOH:CH2Cl2, 2.5:97.5)

Sources & evidence

ORD record
ord-af9c7706be1445f88529b9663e27728e
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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