Hydrazine hydrate (1:1) → HCID 11447902, compound

HRID 1668485Notes

Reaction equation

HRID 1668485 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[CH:8]=[CH:7]2)([O-])=O.O.NN>CO.[Ni]>[N:15]1([CH2:14][CH2:13][N:9]2[C:10]3[C:6](=[CH:5][C:4]([NH2:1])=[CH:12][CH:11]=3)[CH:7]=[CH:8]2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 11403061HCID 11403061, compound

Product 1

HCID 11447902HCID 11447902, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A suspension of compound 94 (250 mg, 0.915 mmol) in dry methanol (10 mL) was treated with Ra—Ni (˜0.05 g) followed by hydrazine hydrate (0.33 mL, 10.7 mmol) and the resulting mixture was refluxed for 20 min. The dark green reaction was cooled to room temperature, filtered through a celite pad, 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, 5:95) to obtain compound 95 (215 mg, 97%) as a yellow oil. 1H NMR (CDCl3) δ 7.16 (d, J=8.7 Hz, 1H), 7.05 (d, J=3.0 Hz, 1H), 6.92 (d, J=2.1 Hz, 1H), 6.67 (dd, J=2.1, 8.7 Hz, 1H), 6.29 (d, J=3.0 Hz, 1H), 4.18 (t, J=7.2 Hz, 2H), 2.67 (t, J=7.5 Hz, 2H), 2.45 (m, 4H), 1.59 (m, 4H); ESI-MS (m/z, %): 244 (M+1).

Workup

  1. temperaturethe resulting mixture was refluxed for 20 min
  2. customThe dark green reaction
  3. filtrationfiltered through a celite pad
  4. washwashed with methanol (2×10 mL)
  5. customThe combined methanol layer was evaporated
  6. customcrude was purified by column chromatography (2 M NH3 in MeOH:CH2Cl2, 5:95)

Sources & evidence

ORD record
ord-a2f51108561b45df88e069bc11392981
Source dataset
uspto-grants-2011_08
Patent number
US07989447B2

Reaction notes

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