Hydrazine hydrate (1:1) → 9-Amino-2,3-Methylenedioxy-5-[2-(N,N-Dimethylamino)Ethyl]-5H-Dibenzo[c,h][1,6]Naphthyridin-6-One

HRID 1611577Notes

Reaction equation

HRID 1611577 reaction equation
[N+:1]([C:4]1[CH:30]=[CH:29][C:7]2[C:8](=[O:28])[N:9]([CH2:23][CH2:24][N:25]([CH3:27])[CH3:26])[C:10]3[C:15]([C:6]=2[CH:5]=1)=[CH:14][N:13]=[C:12]1[CH:16]=[C:17]2[O:22][CH2:21][O:20][C:18]2=[CH:19][C:11]=31)([O-])=O.O.NN>C(O)C.[Ni]>[NH2:1][C:4]1[CH:30]=[CH:29][C:7]2[C:8](=[O:28])[N:9]([CH2:23][CH2:24][N:25]([CH3:27])[CH3:26])[C:10]3[C:15]([C:6]=2[CH:5]=1)=[CH:14][N:13]=[C:12]1[CH:16]=[C:17]2[O:22][CH2:21][O:20][C:18]2=[CH:19][C:11]=31

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 101119799-Nitro-2,3-Methylenedioxy-5-[2-(N,N-Dimethylamino)Ethyl]-5H-Dibenzo[c,h][1,6]Naphthyridin-6-One

Product 1

HCID 110793269-Amino-2,3-Methylenedioxy-5-[2-(N,N-Dimethylamino)Ethyl]-5H-Dibenzo[c,h][1,6]Naphthyridin-6-OneYield 61.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a solution of compound 5a (40 mg, 0.1 mmol) in ethanol (10 mL), Ra—Ni (˜50 mg) and then hydrazine hydrate (0.2 mL) were added and the reaction stirred at room temperature for 3 h. The catalyst was filtered through Celite and filtrate was concentrated in vacuo to provide 23 mg of a solid (61.1% yield); mp 300–301° C.; 1H NMR (CDCl3) δ 2.36 (s, 6H), 3.01 (t, 2H, J=6.6), 4.33 (s, 2H), 4.63 (t, 2H, J=7), 6.18 (s, 2H), 6.91(dd, 1H, J=2.2, 8.8), 7.46 (s, 1H), 7.45 (d, 1H, J=2.2), 7.83 (s, 1H), 8.30 (d, 1H, J=8.8), 9.35 (s, 1H); HRMS m/z calcd for C21H20N4O3H: 377.1614. found 377.1606.

Workup

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

Sources & evidence

ORD record
ord-15aa39519d4e429dbcdfb386557569f0
Source dataset
uspto-grants-2006_01
Patent number
US06989387B2

Reaction notes

Loading…