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

HRID 1479605Notes

Reaction equation

HRID 1479605 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-19c6931511cf41c397e9e12f0caab5db
Source dataset
uspto-grants-2016_08
Patent number
US09408907B2

Reaction notes

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