Pyridine → N-(5-methylpyridin-2-yl)-2-nitrobenzamide

HRID 269722Notes

Reaction equation

HRID 269722 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1.N1C=CC=CC=1.[N+:15]([C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20](Cl)=[O:21])([O-:17])=[O:16]>ClCCl>[N+:15]([C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1)=[O:21])([O-:17])=[O:16]

Participants

5

Reactant 3

HCID 1049PyridineHCID 118752-Nitrobenzoyl chlorideHCID 153482-Amino-5-methylpyridine

Product 1

HCID 840320N-(5-methylpyridin-2-yl)-2-nitrobenzamideYield 52.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 2-amino-5-methylpyridine (3.1 g, 29 mmol) in dichloromethane (200 mL) was added pyridine (7.3 mL, 90 mmol) followed by 2-nitrobenzoyl chloride (5.7 g, 30 mmol). After 4 h, the solvent was removed in vacuo and the residue was partitioned between ethyl acetate (500 mL) and water (250 mL). The organic phase was separated and washed with water, brine, dried (MgSO4) and filtered, and then concentrated in vacuo to a volume of about 100 mL (precipitate observed). The mixture was then sonicated and allowed to stand overnight then filtered. The collected solid was then washed with diethyl ether, filtered and dried under vacuum to give 3.9 g (52%) of the title compound.

Workup

  1. customthe solvent was removed in vacuo
  2. customthe residue was partitioned between ethyl acetate (500 mL) and water (250 mL)
  3. customThe organic phase was separated
  4. washwashed with water, brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo to a volume of about 100 mL (precipitate observed)
  8. customThe mixture was then sonicated
  9. waitto stand overnight
  10. filtrationthen filtered
  11. washThe collected solid was then washed with diethyl ether
  12. filtrationfiltered
  13. customdried under vacuum

Sources & evidence

ORD record
ord-5d926ab8217a4626b66edd9e0faf98cb
Source dataset
uspto-grants-2008_11
Patent number
US07449457B2

Reaction notes

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