HCID 60046925, compound → HCID 60046928, compound

HRID 1672337Notes

Reaction equation

HRID 1672337 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:17]=2)[N:12]=[CH:11][C:10]=1[N+:25]([O-])=O>CO.C1COCC1.[Ni]>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:17]=2)[N:12]=[CH:11][C:10]=1[NH2:25]

Participants

4

Reactant 1

HCID 60046925HCID 60046925, compound

Product 1

HCID 60046928HCID 60046928, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

The title compound is prepared in analogy to Example 19e by hydrogenation at 0° C. for 86 min starting from 0.697 g (1.502 mmol) of (2-bromo-phenyl)-(3-nitro-6-phenyl-quinolin-4-yl)-amine (Example 53e) and 0.25 g Raney-Ni in 25 ml methanol-THF 2:1. Purification follows by chromatography on silica gel (ethyl acetate-hexane 1:1). mp: 174-177° C.; MS: 390 (M++1); HPLC: tret=10.50 min (Grad 1).

Workup

  1. customPurification
  2. customtret=10.50 min (Grad 1)

Sources & evidence

ORD record
ord-336b9de8dedb49e7b7bb987baa85b142
Source dataset
uspto-grants-2011_08
Patent number
US07998972B2

Reaction notes

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