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

HRID 1882918Notes

Reaction equation

HRID 1882918 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>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:20](=[O:21])[C:19]2[CH:23]=[CH:24][CH:25]=[CH:26][C:18]=2[N+:15]([O-:17])=[O:16])=[N:3][CH:4]=1

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) and pyridine (7.3 mL, 90 mmol) in dichloromethane (200 mL) was added 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 again with water (250 mL) followed by brine (250 mL) and then dried with MgSO4, filtered and partially concentrated in vacuo, which resulted in the formation of a precipitate. After standing overnight, the solid was filtered and dried in vacuo to give 3.9 g (52%) of white solid.

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 again with water (250 mL)
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationpartially concentrated in vacuo, which
  8. customresulted in the formation of a precipitate
  9. waitAfter standing overnight
  10. filtrationthe solid was filtered
  11. customdried in vacuo

Sources & evidence

ORD record
ord-49c3645d827f48519d0558775768d333
Source dataset
uspto-grants-2004_07
Patent number
US06759414B2

Reaction notes

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