Hydrazine hydrate (1:1) → HCID 11025207, compound

HRID 1611579Notes

Reaction equation

HRID 1611579 reaction equation
[N+:1]([C:4]1[C:17]2[C:16]3[C:11](=[C:12]4[CH:21]=[C:20]5[O:22][CH2:23][O:24][C:19]5=[CH:18][C:13]4=[N:14][CH:15]=3)[N:10]([CH2:25][CH2:26][N:27]([CH3:29])[CH3:28])[C:9](=[O:30])[C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-])=O.O.NN>C(O)C.[Ni]>[NH2:1][C:4]1[C:17]2[C:16]3[C:11](=[C:12]4[CH:21]=[C:20]5[O:22][CH2:23][O:24][C:19]5=[CH:18][C:13]4=[N:14][CH:15]=3)[N:10]([CH2:25][CH2:26][N:27]([CH3:28])[CH3:29])[C:9](=[O:30])[C:8]=2[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 11729193HCID 11729193, compound

Product 1

HCID 11025207HCID 11025207, compoundYield 74.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a solution of compound 6a (40 mg, 0.1 mmol) in ethanol (10 mL), Ra—Ni (˜50 mg) and then hydrazine hydrate (0.2 mL) were added and reaction was stirred at room temperature for 3 h. The catalyst was filtered through the Celite and filtrate was concentrated in vacuo to provide 28 mg of a solid (74.4% yield); mp 223–224° C.; 1H NMR (CDCl3) δ 2.31 (s, 6H), 2.90 (t, 2H, J=7), 4.34 (s, 2H), 4.65 (t, 2H, J=7.4), 6.18 (s, 2H,), 7.16 (d, 1H, J=8), 7.4 (dd, 2H, J=7.6, 9.8) 7.74 (s, 1H), 8.02 (d, 1H, J=7.8), 10.03 (s, 1H); HRMS m/z calcd for C21H20N4O3H: 377.1614. found 377.1631.

Workup

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

Sources & evidence

ORD record
ord-0c266f5ce24a455c9f3160bc8572774e
Source dataset
uspto-grants-2006_01
Patent number
US06989387B2

Reaction notes

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