Hydrazine hydrate (1:1) → HCID 56593856, compound

HRID 1668491Notes

Reaction equation

HRID 1668491 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([C:8]([C:13]3[CH:18]4[CH2:19][CH2:20][N:15]([CH2:16][CH2:17]4)[CH:14]=3)=[CH:9][NH:10]2)=[CH:6][CH:5]=1)([O-])=O.O.NN>CO.[Ni]>[N:15]12[CH2:16][CH2:17][CH:18]([CH2:19][CH2:20]1)[C:13]([C:8]1[C:7]3[C:11](=[CH:12][C:4]([NH2:1])=[CH:5][CH:6]=3)[NH:10][CH:9]=1)=[CH:14]2

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 56593710HCID 56593710, compound

Product 1

HCID 56593856HCID 56593856, compoundYield 98.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Compound 109 (0.4 g, 1.485 mmol) in dry methanol (10 mL) was treated with Ra—Ni (˜0.05 g) and hydrazine hydrate (0.46 mL, 1.029 mmol). The resulting mixture was placed in a pre-heated oil bath and refluxed for 2 min (until yellow colour disappears). The reaction was brought to room temperature, filtered through celite bed and washed with methanol (3×10 mL). The combined methanol layer was evaporated and crude was purified by column chromatography (2M NH3 in MeOH:CH2Cl2, 1:9) to obtain compound 110 (0.35 g, quantitative) as a foam. mp 65-67° C.; 1H NMR (DMSO-d6) δ 1.42-1.54 (m, 2H), 1.62-1.74 (m, 2H), 2.52-2.56 (m, 2H), 2.86-2.94 (m, 2H), 2.98-3.02 (m, 1H), 4.75 (s, 2H), 6.41 (dd, 1H, J=2.1, 8.4 Hz), 6.53 (d, 1H, J=1.8 Hz), 6.69 (s, 1H), 7.16 (d, 1H, J=2.4 Hz), 7.35 (d, 1H, J=8.4 Hz), 10.57 (s, 1H); ESI-MS (m/z, %): 240 (MH+, 100).

Workup

  1. customThe resulting mixture was placed in a pre-heated oil bath
  2. temperaturerefluxed for 2 min (until yellow colour disappears)
  3. customwas brought to room temperature
  4. filtrationfiltered through celite bed
  5. washwashed with methanol (3×10 mL)
  6. customThe combined methanol layer was evaporated
  7. customcrude was purified by column chromatography (2M NH3 in MeOH:CH2Cl2, 1:9)

Sources & evidence

ORD record
ord-f4efd3e9d8444350b3c0cf8e6e889d35
Source dataset
uspto-grants-2011_08
Patent number
US07989447B2

Reaction notes

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