4-Chloro-N-methylpicolinamide → HCID 86594690, compound

HRID 491638Notes

Reaction equation

HRID 491638 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([N+:11]([O-:13])=[O:12])=[CH:4][C:3]=1[OH:14].[CH3:15][NH:16][C:17]([C:19]1[CH:24]=[C:23](Cl)[CH:22]=[CH:21][N:20]=1)=[O:18]>C(Cl)Cl>[CH3:15][NH:16][C:17]([C:19]1[CH:24]=[C:23]([O:14][C:3]2[CH:4]=[C:5]([N+:11]([O-:13])=[O:12])[C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=2[CH3:1])[CH:22]=[CH:21][N:20]=1)=[O:18]

Participants

4

Reactant 2

HCID 14768144-Chloro-N-methylpicolinamideHCID 10313539HCID 10313539, compound

Product 1

HCID 86594690HCID 86594690, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
170 °C

Procedure

2-Methyl-4,5-dinitrophenol (Step A, 1.34 g, 6.77 mmol) and 4-chloro-pyridine-2-carboxylic acid methylamide (1.16 g, 6.77 mmol) were combined and heated at 160-180° C. (round bottom flask with condenser). The reaction was cooled to RT, the contents of the flask were dissolved in CH2Cl2 and the organic layer washed with 2 N NaOH, then water. The organic layer was dried with Na2SO4, filtered and evaporated. The mixture was purified by column chromatography using EtOAc/hexanes as the eluant. The title compound was obtained as a tan solid.

Workup

  1. temperatureThe reaction was cooled to RT
  2. washthe organic layer washed with 2 N NaOH
  3. dry with materialThe organic layer was dried with Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe mixture was purified by column chromatography

Sources & evidence

ORD record
ord-47bf3f53b6c242fd8ffea5d0968768fc
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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