Hydrazine hydrate (1:1) → HCID 11047052, compound

HRID 1611575Notes

Reaction equation

HRID 1611575 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[C:16]3[C:11](=[C:12]4[CH:20]=[C:19]5[O:21][CH2:22][O:23][C:18]5=[CH:17][C:13]4=[N:14][CH:15]=3)[N:10]([CH2:24][CH2:25][N:26]([CH3:28])[CH3:27])[C:9](=[O:29])[C:8]=2[CH:30]=1)([O-])=O.O.NN>C(O)C.[Ni]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]2[C:16]3[C:11](=[C:12]4[CH:20]=[C:19]5[O:21][CH2:22][O:23][C:18]5=[CH:17][C:13]4=[N:14][CH:15]=3)[N:10]([CH2:24][CH2:25][N:26]([CH3:27])[CH3:28])[C:9](=[O:29])[C:8]=2[CH:30]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 9801436HCID 9801436, compound

Product 1

HCID 11047052HCID 11047052, compoundYield 69.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a solution of compound 4a (40 mg, 0.1 mmol) in ethanol (10 mL), Ra—Ni (˜50 mg) then hydrazine hydrate (0.2 mL) were added and the reaction stirred at room temperature for 3 h. The catalyst was filtered through the Celite and filtrate was concentrated in vacuo to provide 26 mg of a solid (69.1% yield); mp 245–246° C.; 1H NMR (CDCl3) δ 2.36 (s, 6H), 3.01 (t, 2H, J=7.4), 4.11(s, 2H), 4.68 (t, 2H, J=7.4), 6.17(s, 2H,), 7.18 (dd, 1H, J=2.8, 11.4), 7.46 (s, 1H) 7.71 (d, 1H, J=3), 7.80 (s, 1H) 8.20 (d, 1H, J=8.8), 9.40 (s, 1H); HRMS m/z calcd for C21H20N4O3H: 377.1614. found 377.1604.

Workup

  1. filtrationThe catalyst was filtered through the Celite and filtrate
  2. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-635857b9ecd145a1aa85911cd507e1fa
Source dataset
uspto-grants-2006_01
Patent number
US06989387B2

Reaction notes

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