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

HRID 1922354Notes

Reaction equation

HRID 1922354 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[CH2:21][CH2:20][CH2:19][CH2:18]1)[C:9](=[O:22])[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]1)[C:9](=[O:22])[CH2:8][CH2:7]2

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 533922596-nitro-1-(3-(pyrrolidin-1-yl)propyl)-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 533922616-amino-1-(3-(pyrrolidin-1-yl)propyl)-3,4-dihydroquinolin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

6-nitro-1-(3-(pyrrolidin-1-yl)propyl)-3,4-dihydroquinolin-2(1H)-one (89 mg, 0.293 mmol) in dry methanol (5 mL) was treated with Ra—Ni (˜0.05 g) followed by hydrazine hydrate (92 uL, 2.95 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: 58 mg of yellow oil (73%). 1H NMR (CDCl3) δ: 6.86 (d, J=8.4 Hz, 1H), 6.55 (dd, J=2.7, 8.4 Hz, 1H), 6.52 (d, J=2.1 Hz, 1H), 3.94 (m, 2H), 2.81-2.76 (m, 2H), 2.61-2.56 (m, 2H), 2.53-2.49 (m, 6H), 1.87-1.82 (m, 2H), 1.79-1.75 (m, 4H). MS (ESI): 274.2 (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-1178f2463d1e4536b0546c076ce9c1c3
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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