4-Methyl-3-nitrobenzoic acid → HCID 896862, compound

HRID 2415709Notes

Reaction equation

HRID 2415709 reaction equation
[C:1]([Cl:6])(=O)[C:2]([Cl:4])=O.[N+:7]([C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][C:18]=1[CH3:19])[C:13]([OH:15])=O)([O-:9])=[O:8]>C(Cl)Cl.CN(C=O)C>[Cl:4][C:2]1[CH:19]=[C:18]([CH:17]=[CH:16][C:1]=1[Cl:6])[CH2:10][NH:7][C:13](=[O:15])[C:12]1[CH:16]=[CH:17][C:18]([CH3:19])=[C:10]([N+:7]([O-:9])=[O:8])[CH:11]=1

Participants

5

Reactant 2

HCID 73194-Methyl-3-nitrobenzoic acidHCID 65578Oxalyl chloride

Product 1

HCID 896862HCID 896862, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (4.8 ml) was added to a solution of 3-nitro-4-methylbenzoic acid (9.06 g) in methylene chloride (100 ml) and DMF (a few drops) and the reaction stirred at ambient temperature for 16 hours. The reaction mixture was evaporated and the residue was dissolved in methylene chloride (100 ml). 3,4-Dichlorobenzylamine (7.04 g), 4-dimethylaminopyridine (0.31 g) and triethylamine (13.9 ml) were added and the reaction mixture was stirred at ambient temperature for 16 hours. The mixture was washed with a saturated aqueous sodium bicarbonate solution, dried over magnesium sulphate and evaporated. The residue was purified by column chromatography using a 250:8:1 mixture of methylene chloride, methanol and a saturated aqueous ammonium chloride solution as eluent to give N-(3,4-dichlorobenzyl)4-methyl-3-nitrobenzamide as a solid (9.95 g); NMR Spectrum: (DMSOd6) 2.57 (s, 3H), 4.47 (d, 2H), 7.31 (m, 1H), 7.56 (m, 2H), 7.61 (d, 1H), 8.1 (m, 1H), 8.47 (d, 1H), 9.3 (t, 1H).

Workup

  1. customThe reaction mixture was evaporated
  2. dissolutionthe residue was dissolved in methylene chloride (100 ml)
  3. addition3,4-Dichlorobenzylamine (7.04 g), 4-dimethylaminopyridine (0.31 g) and triethylamine (13.9 ml) were added
  4. stirringthe reaction mixture was stirred at ambient temperature for 16 hours
  5. washThe mixture was washed with a saturated aqueous sodium bicarbonate solution
  6. dry with materialdried over magnesium sulphate
  7. customevaporated
  8. customThe residue was purified by column chromatography
  9. additiona 250:8:1 mixture of methylene chloride, methanol

Sources & evidence

ORD record
ord-1e3b89d706814b29b16a039628901c7c
Source dataset
uspto-grants-2004_11
Patent number
US06821965B1

Reaction notes

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