Dichloromethane → 3-Chlorobenzo[f][1,7]naphthyridine-5,8-diamine

HRID 340318Notes

Reaction equation

HRID 340318 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.C(Cl)[Cl:20]>[Ni].CCO>[Cl:20][C:11]1[CH:10]=[CH:9][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]=1

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 668916908-Nitrobenzo[f][1,7]naphthyridin-5-amine

Product 1

HCID 582134793-Chlorobenzo[f][1,7]naphthyridine-5,8-diamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

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 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 purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-100% EtOAc/Hexanes to give 3-chlorobenzo[f][1,7]naphthyridine-5,8-diamine as a white solid. 1H NMR (methanol-d4): δ 8.75 (d, 1H), 8.08 (dd, 1H), 7.70 (d, 1H), 6.84-6.81 (m, 2H). LRMS [M+H]=245.1.

Workup

  1. filtrationThe insoluble solid was filtered off through celite
  2. concentrationthe filtrate was concentrated en vacuo
  3. customto obtain a crude residue
  4. customThe crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO)

Sources & evidence

ORD record
ord-f7d35e54fdf6408c9f4ece476f5a455d
Source dataset
uspto-grants-2014_11
Patent number
US08895577B2

Reaction notes

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