Hydrazine hydrate (1:1) → HCID 59807111, compound

HRID 1922352Notes

Reaction equation

HRID 1922352 reaction equation
[CH2:1]([N:3]([CH2:21][CH3:22])[CH2:4][CH2:5][CH2:6][N:7]1[C:16]2[C:11](=[CH:12][C:13]([N+:17]([O-])=O)=[CH:14][CH:15]=2)[CH2:10][CH2:9][C:8]1=[O:20])[CH3:2].O.NN>CO.[Ni]>[NH2:17][C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[N:7]([CH2:6][CH2:5][CH2:4][N:3]([CH2:21][CH3:22])[CH2:1][CH3:2])[C:8](=[O:20])[CH2:9][CH2:10]2

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 59807123HCID 59807123, compound

Product 1

HCID 59807111HCID 59807111, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

1-(3- (Diethylamino)propyl)-6-nitro-3,4-dihydroquinolin-2(1H)-one (93 mg, 0.305 mmol) in dry methanol (5 mL) was treated with Ra—Ni (slurry in water, ˜0.05 g) followed by hydrazine hydrate (95 uL, 3.05 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: 62 mg of yellow oil (74%). 1H NMR (CDCl3) δ: 6.87 (d, J=8.4 Hz, 1H), 6.56 (dd, J=2.7, 8.4 Hz, 1H), 6.52 (d, J=2.1 Hz, 1H), 3.91 (m, 2H), 2.81-2.76 (m, 2H), 2.61-2.54 (m, 2H), 2.52-2.46 (m, 6H), 1.78-1.61 (m, 2H), 1.01 (t, J=7.2 Hz, 6H). MS (ESI): 276.2 (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-ad8aa35e3c4843809dd9053eec71d880
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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