8-Nitrobenzo[f][1,7]naphthyridin-5-amine → Benzo[f][1,7]naphthyridine-5,8-diamine

HRID 340315Notes

Reaction equation

HRID 340315 reaction equation
[N+:1]([C:4]1[CH:18]=[CH:17][C:7]2=[C:8]3[C:13](=[C:14]([NH2:16])[N:15]=[C:6]2[CH:5]=1)[N:12]=[CH:11][CH:10]=[CH:9]3)([O-])=O>[Ni].CCO.N.C(Cl)Cl>[CH:9]1[C:8]2[C:13](=[C:14]([NH2:16])[N:15]=[C:6]3[CH:5]=[C:4]([NH2:1])[CH:18]=[CH:17][C:7]3=2)[N:12]=[CH:11][CH:10]=1

Participants

5

Reactant 1

HCID 668916908-Nitrobenzo[f][1,7]naphthyridin-5-amine

Product 1

HCID 58213735Benzo[f][1,7]naphthyridine-5,8-diamine

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 6344DichloromethaneSolventHCID 22020343Ethanol, reaction products with ammonia, distn. residuesSolvent

Procedure

A mixture of 8-nitrobenzo[f][1,7]naphthyridin-5-amine (from the previous step) (1.0 eq) and Raney Nickel (wet, 10% wt) in EtOH/ammonia (2:1) was stirred under H2 balloon overnight. The reaction mixture was diluted with DCM. The insoluble solid was filtered off through celite, and the filtrate was concentrated en vacuo to obtain a crude residue. The crude material was washed with 10% MeOH/DCM and 70% EtOAc/Hexanes to give benzo[f][1,7]naphthyridine-5,8-diamine as an off white solid: 1H NMR (methanol-d4): δ 8.97 (dd, 1H), 8.90 (dd, 1H), 8.41 (d, 1H), 7.83 (dd, 1H), 7.57 (d, 1H), 7.39 (dd, 1H), 3.96 (s, 2). LRMS [M+H]=229.1.

Workup

  1. filtrationThe insoluble solid was filtered off through celite
  2. concentrationthe filtrate was concentrated en vacuo
  3. customto obtain a crude residue
  4. washThe crude material was washed with 10% MeOH/DCM and 70% EtOAc/Hexanes

Sources & evidence

ORD record
ord-cd32b35f70fc4736998861954f9e4359
Source dataset
uspto-grants-2014_11
Patent number
US08895577B2

Reaction notes

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