Pyridine → HCID 86660391, compound

HRID 1406513Notes

Reaction equation

HRID 1406513 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[C:7](Cl)=[O:8])([O-:3])=[O:2].[NH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[CH:19][N:18]=1.N1C=CC=CC=1>C1(C)C=CC=CC=1>[C:23]([C:20]1[CH:21]=[CH:22][C:17]([NH:16][C:7](=[O:8])[C:6]2[CH:10]=[CH:11][C:12]([N+:13]([O-:15])=[O:14])=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)=[N:18][CH:19]=1)#[N:24]

Participants

5

Reactant 3

HCID 1049PyridineHCID 8182602-Amino-5-cyanopyridineHCID 118064913,4-dinitrobenzoyl Chloride

Product 1

HCID 86660391HCID 86660391, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3,4-Dinitro-benzoyl chloride (0.69 g, 3.0 mmol) in 2 mL toluene was added to a stirred mixture of 2-amino-5-cyanopyridine (0.357 g, 3.0 mmol) and 5 mL pyridine. After stirring overnight at ambient temperature the mixture was concentrated i.vac. The residue was taken up in ethyl acetate and 5% NaHCO3 (aq). The organic layer was washed with water and brine, separated, dried and concentrated i.vac. The residue was purified by chromatography on silica gel (eluent gradient: dichloromethane/ethanol=100:0->100:2).

Workup

  1. concentrationwas concentrated i.vac
  2. washThe organic layer was washed with water and brine
  3. customseparated
  4. customdried
  5. concentrationconcentrated i.vac
  6. customThe residue was purified by chromatography on silica gel (eluent gradient: dichloromethane/ethanol=100:0->100:2)

Sources & evidence

ORD record
ord-46d7386e27884eba832f23ad589076e4
Source dataset
uspto-grants-2014_12
Patent number
US08916599B2

Reaction notes

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