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

HRID 1259182Notes

Reaction equation

HRID 1259182 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-bbb0ec13a42a48b5b0c69579690b42d2
Source dataset
uspto-grants-2013_06
Patent number
US08466167B2

Reaction notes

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