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

HRID 1259186Notes

Reaction equation

HRID 1259186 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 vaccuo 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 vaccuo
  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-8c8df2a114e54a4f83f41435ab4e471f
Source dataset
uspto-grants-2013_06
Patent number
US08466167B2

Reaction notes

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