Hydrazine hydrate (1:1) → 462649-11-2

HRID 1668483Notes

Reaction equation

HRID 1668483 reaction equation
[CH3:1][N:2]([CH3:17])[CH2:3][CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([N+:14]([O-])=O)=[CH:11][CH:12]=2)[CH:7]=[CH:6]1.O.NN>CO.[Ni]>[CH3:1][N:2]([CH3:17])[CH2:3][CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([NH2:14])=[CH:11][CH:12]=2)[CH:7]=[CH:6]1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 11424796HCID 11424796, compound

Product 1

HCID 11206483462649-11-2Yield 55%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A suspension of compound 91 (250 mg, 1.07 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 92(119 mg, 55%) 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), 6.30 (d, J=3.0 Hz, 1H), 4.17 (t, J=7.2 Hz, 2H), 2.68 (t, J=7.5 Hz, 2H), 2.29 (s, 6H); ESI-MS (m/z, %): 204 (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-0074ff050f9548fdb410df008e90f33c
Source dataset
uspto-grants-2011_08
Patent number
US07989447B2

Reaction notes

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