Hydrazine hydrate (1:1) → HCID 59807147, compound

HRID 1922347Notes

Reaction equation

HRID 1922347 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][CH2:9][N:10]2[C:19]3[C:14](=[CH:15][C:16]([N+:20]([O-])=O)=[CH:17][CH:18]=3)[CH2:13][CH2:12][C:11]2=[O:23])[CH2:3][CH2:2]1.O.NN>CO.[Ni]>[NH2:20][C:16]1[CH:15]=[C:14]2[C:19](=[CH:18][CH:17]=1)[N:10]([CH2:9][CH2:8][CH2:7][N:4]1[CH2:3][CH2:2][O:1][CH2:6][CH2:5]1)[C:11](=[O:23])[CH2:12][CH2:13]2

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 59807103HCID 59807103, compound

Product 1

HCID 59807147HCID 59807147, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

1-(3-morpholinopropyl)-6-nitro-3,4-dihydroquinolin-2(1H)-one (78 mg, 0.244 mmol) in dry methanol (5 mL) was treated with Ra—Ni (˜0.05 g) followed by hydrazine hydrate (76 uL, 2.44 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 and the 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: 64 mg of yellow oil (90%). 1H NMR (CDCl3) δ: 6.86 (d, J=8.4 Hz, 1H), 6.56 (dd, J=2.7, 8.4 Hz, 1H), 6.52 (d, J=2.1 Hz, 1H), 3.93 (t, J=7.2 Hz, 2H), 3.71 (t, J=4.5 Hz, 4H), 2.81-2.76 (m, 2H), 2.61-2.56 (m, 2H), 2.44-2.36 (m, 6H) 1.83-1.65 (m, 2H). MS (ESI): 290.2 (M+1).

Workup

  1. temperaturethe resulting mixture was refluxed for 30 minutes
  2. filtrationfiltered through a celite bed
  3. washthe bed washed 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-f5e10c8143ae46c09d03883783f4ce0e
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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