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

HRID 1479600Notes

Reaction equation

HRID 1479600 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>CCO.C(Cl)Cl.[Pd]>[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 23938PalladiumCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 8-nitrobenzo[f][1,7]naphthyridin-5-amine (from the previous step) (1.0 eq) and Pd/C (wet, 10% wt) in EtOH 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 vaccuo to obtain a crude residue. The crude material was washed with acetone to give benzo[f][1,7]naphthyridine-5,8-diamine as an off white solid: 1H NMR (methanol-d4): δ 8.73 (dd, 1H), 8.71 (dd, 1H), 8.11 (d, 1H), 7.69 (dd, 1H), 6.86 (d, 1H), 6.82 (dd, 1H). LRMS [M+H]=211.1.

Workup

  1. filtrationThe insoluble solid was filtered off through celite
  2. concentrationthe filtrate was concentrated en vaccuo
  3. customto obtain a crude residue
  4. washThe crude material was washed with acetone

Sources & evidence

ORD record
ord-95e78f4f077d43028a7836734d39ffb8
Source dataset
uspto-grants-2016_08
Patent number
US09408907B2

Reaction notes

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