1,2-Dichloroethane → 2-Fluoro-n-methoxy-n-methyl-4-nitrobenzamide

HRID 2265104Notes

Reaction equation

HRID 2265104 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](O)=[O:9])=[C:6]([F:13])[CH:5]=1)([O-:3])=[O:2].Cl.[CH3:15][NH:16][O:17][CH3:18].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>N1C=CC=CC=1>[CH3:18][O:17][N:16]([CH3:15])[C:8](=[O:9])[C:7]1[CH:11]=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]=1[F:13]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 3026792-Fluoro-4-nitrobenzoic acid

Product 1

HCID 231065432-Fluoro-n-methoxy-n-methyl-4-nitrobenzamideYield 85.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
60 °C

Procedure

4-Nitro-2-fluorobenzoic acid (5.03 g) was dissolved in pyridine (60.0 ml), and N,O-dimethylhydroxylamine hydrochloride (7.95 g), HOBt (5.50 g), and EDC (7.79 g) were added thereto. The obtained mixture was stirred at 60° C. for 15 hours. After the reaction mixture was allowed to cool, the solvent was distilled off under reduced pressure. Water and ethyl acetate were added to the obtained residue, and extraction and washing were carried out. The organic layer was sequentially washed with a 1N hydrochloric acid aqueous solution, saturated sodium-bicarbonate aqueous solution, and saturated sodium chloride solution, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was recrystallized with a mixed solvent of tert-butylmethylether and n-heptane to obtain Compound 14a (5.28 g, 85%) as an opalescent solid.

Workup

  1. temperatureto cool
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionWater and ethyl acetate were added to the obtained residue, and extraction
  4. washwashing
  5. washThe organic layer was sequentially washed with a 1N hydrochloric acid aqueous solution, saturated sodium-bicarbonate aqueous solution, and saturated sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customThe residue was recrystallized with a mixed solvent of tert-butylmethylether and n-heptane

Sources & evidence

ORD record
ord-62f9dad4f083430e91d1cb1f3a28fac0
Source dataset
uspto-grants-2010_12
Patent number
US07855300B2

Reaction notes

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