Triethylamine → N-methoxy-N,3-dimethyl-4-nitrobenzamide

HRID 928779

Reaction equation

HRID 928779 reaction equation
C(N(CC)CC)C.[CH3:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[N+:18]([O-:20])=[O:19])[C:12](O)=[O:13].Cl.[CH3:22][NH:23][O:24][CH3:25].CCN=C=NCCCN(C)C>C(Cl)Cl>[CH3:25][O:24][N:23]([CH3:22])[C:12](=[O:13])[C:11]1[CH:15]=[CH:16][C:17]([N+:18]([O-:20])=[O:19])=[C:9]([CH3:8])[CH:10]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 183703-Methyl-4-nitrobenzoic acidHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

Product 1

HCID 46318653N-methoxy-N,3-dimethyl-4-nitrobenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (7.6 mL, 54.651 mmol) was added slowly to a mixture of 3-methyl-4-nitrobenzoic acid (5 g, 27.326 mmol), N,O-dimethylhydroxylamine hydrochloride (2.99 g, 30.058 mmol), and EDCI (6.28 g, 32.791 mmol) in DCM (30 mL). The mixture was stirred at room temperature overnight, quenched with saturated aqueous NaHCO3 and stirred at room temperature for 30 minutes. Water (50 mL) was added followed by additional DCM. The mixture was stirred for 10 minutes and layers were separated. The aqueous layer was again extracted with DCM. The combined organic layer was dried over Na2SO4, then filtered. The solvent was removed and the residual oil chromatographed (DCM/EtOAc) to provide the product as a white solid.

Workup

  1. customquenched with saturated aqueous NaHCO3
  2. stirringstirred at room temperature for 30 minutes
  3. additionWater (50 mL) was added
  4. stirringThe mixture was stirred for 10 minutes
  5. customlayers were separated
  6. extractionThe aqueous layer was again extracted with DCM
  7. dry with materialThe combined organic layer was dried over Na2SO4
  8. filtrationfiltered
  9. customThe solvent was removed
  10. customthe residual oil chromatographed (DCM/EtOAc)

Sources & evidence

ORD record
ord-2fb12c1d506d4d4085f4b4e897e9d261
Source dataset
uspto-grants-2016_03
Patent number
US09290476B2

Linked notes

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