Benzoyl chloride, 3-nitro- → HCID 46561113, compound

HRID 642126Notes

Reaction equation

HRID 642126 reaction equation
[NH2:1][CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1.[N+:13]([C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=1)[C:19](Cl)=[O:20])([O-:15])=[O:14]>C(Cl)Cl>[N+:13]([C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=1)[C:19]([NH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:11][CH:12]=1)=[O:20])([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 8495Benzoyl chloride, 3-nitro-HCID 571728Methyl 4-(aminomethyl)benzoate

Product 1

HCID 46561113HCID 46561113, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Under an inert atmosphere, to a stirred solution of methyl 4-(aminomethyl)benzoate (50 g, 0.436 mol) and TEA (210 mL, 1.5 mol) in anhydrous DCM (1.0 L) was added a solution of freshly prepared 3-nitro benzoyl chloride (0.59 mol) in DCM (250 mL). The resulting mixture was allowed to stir for 2 hrs. The reaction was quenched with a 10% aqueous solution of sodium hydrogenocarbonate. The organic layer was washed with a 1.5N HCl solution and water. After drying over MgSO4 and evaporation of the solvent in vacuo, a solid was obtained and purified by flash chromatography to give the title compound (50 g) in a 52% yield as a white powder.

Workup

  1. customThe reaction was quenched with a 10% aqueous solution of sodium hydrogenocarbonate
  2. washThe organic layer was washed with a 1.5N HCl solution and water
  3. dry with materialAfter drying over MgSO4 and evaporation of the solvent in vacuo
  4. customa solid was obtained
  5. custompurified by flash chromatography

Sources & evidence

ORD record
ord-3ac499fa42844857b03f4922dae0ac9a
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

Loading…