4-Nitrobenzoic Acid → N-(2-methoxyphenyl)-4-nitrobenzamide

HRID 2421

Reaction equation

HRID 2421 reaction equation
Cl.CN(C)CCCN=C=NCC.[CH3:13][O:14][C:15]1[C:16]([NH2:21])=[CH:17][CH:18]=[CH:19][CH:20]=1.[N+:22]([C:25]1[CH:33]=[CH:32][C:28]([C:29](O)=[O:30])=[CH:27][CH:26]=1)([O-:24])=[O:23].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[N+:22]([C:25]1[CH:26]=[CH:27][C:28]([C:29]([NH:21][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[O:14][CH3:13])=[O:30])=[CH:32][CH:33]=1)([O-:24])=[O:23]

Participants

6

Reactant 4

HCID 61084-Nitrobenzoic AcidHCID 70002-MethoxyanilineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 774513N-(2-methoxyphenyl)-4-nitrobenzamideYield 87.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

With cooling in an ice bath, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC.HCl) (630 mg, 3.29 mmol) was added to 15 ml of methylene chloride solution containing o-anisidine (368 mg, 2.99 mmol) and 4-nitrobenzoic acid (500 mg, 2.99 mmol). After 1 hour of stirring at the same temperature, the reaction mixture was roughly adjusted to pH 8 with saturated sodium bicarbonate aqueous solution, extracted with methylene chloride and then washed with water and saturated brine in that order. After drying on anhydrous magnesium sulfate, the solvent was removed by evaporation, and the resulting solid material was purified by silica gel column chromatography (methylene chloride) to obtain 712 mg (87.4%) of the title compound in the form of yellow powder.

Workup

  1. temperatureWith cooling in an ice bath
  2. extractionextracted with methylene chloride
  3. washwashed with water and saturated brine in that order
  4. dry with materialAfter drying on anhydrous magnesium sulfate
  5. customthe solvent was removed by evaporation
  6. customthe resulting solid material was purified by silica gel column chromatography (methylene chloride)

Sources & evidence

ORD record
ord-c4ba4a81e15b4995a5093c01878efc4c
Source dataset
uspto-grants-1998_03
Patent number
US05728835

Linked notes

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