Pyridine → HCID 21948814, compound

HRID 2215404Notes

Reaction equation

HRID 2215404 reaction equation
CN[C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:13]([O-:15])=[O:14])[N:4]=1.[N:16]1[CH:21]=CC=CC=1.[C:22](OC(=O)C)(=[O:24])[CH3:23].C([O-])(O)=O.[Na+]>C(OCC)(=O)C>[C:22]([C:3]1[C:12]([NH:16][CH3:21])=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:13]([O-:15])=[O:14])[N:4]=1)(=[O:24])[CH3:23]

Participants

6

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 21948796N-Methyl-5-nitro-2-quinolinamine

Product 1

HCID 21948814HCID 21948814, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

580 mg (2.4 mmol) of 2-methylamino-5-nitroquinoline is stirred with 4 ml (50 mmol) of pyridine and 2 ml (21 mmol) of acetic anhydride for 15 hours at room temperature and stirred for 4.5 hours at 60° C. The batch is diluted with ethyl acetate, poured into saturated NaHCO3 solution, stirred for 30 minutes, and extracted with ethyl acetate. The extracts are dried (Na2SO4) and concentrated by evaporation. The residue is purified on silica gel with hexane-ethyl acetate: 660 mg of a yellow solid.

Workup

  1. stirringstirred for 30 minutes
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extracts are dried (Na2SO4)
  4. concentrationconcentrated by evaporation
  5. customThe residue is purified on silica gel with hexane-ethyl acetate

Sources & evidence

ORD record
ord-6bfba9e84bf04d0e97b9beaf4f42907e
Source dataset
uspto-grants-2006_09
Patent number
US07109212B2

Reaction notes

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