Pyridine → N,3,4,5-tetramethoxy-N-methyl-Benzamide

HRID 1757502Notes

Reaction equation

HRID 1757502 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([O:14][CH3:15])[C:11]=1[O:12][CH3:13])[C:6](Cl)=[O:7].Cl.[CH3:17][NH:18][O:19][CH3:20].N1C=CC=CC=1>C(O)C>[CH3:20][O:19][N:18]([CH3:17])[C:6](=[O:7])[C:5]1[CH:4]=[C:3]([O:2][CH3:1])[C:11]([O:12][CH3:13])=[C:10]([O:14][CH3:15])[CH:9]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

Product 1

HCID 267535N,3,4,5-tetramethoxy-N-methyl-BenzamideYield 97.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve 3,4,5-trimethoxybenzoyl chloride (2.3 g, 10 mmol) and N,O-dimethylhydroxylamine hydrochloride (1.10 g, 11 mmol) in ethanol-free chloroform at room temperature. Cool the solution to 0° C. and add pyridine (1.85 g, 22 mmol). Stir at ambient temperature for 1 hour and evaporate the solvent in vacuo. Partition the residue between aqueous sodium chloride and a 1:1 mixture of ethyl ether and methylene chloride. Separate the organic phase, dry (Na2SO4), and evaporate the solvent in vacuo to yield an oil. Filter the oil through silica gel eluting with 65% ethyl acetate/hexane to yield 2.5 g of N-methoxy-N-methyl-(3,4,5-trimethoxy)benzamide.

Workup

  1. customevaporate the solvent in vacuo
  2. customPartition the residue between aqueous sodium chloride
  3. additiona 1:1 mixture of ethyl ether and methylene chloride
  4. customSeparate the organic phase
  5. dry with materialdry (Na2SO4)
  6. customevaporate the solvent in vacuo
  7. customto yield an oil
  8. filtrationFilter the oil through silica gel eluting with 65% ethyl acetate/hexane

Sources & evidence

ORD record
ord-b069b36463db499283f63e20862fef94
Source dataset
uspto-grants-1995_08
Patent number
US05446068

Reaction notes

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