Pyridine → HCID 835412, compound

HRID 1094970Notes

Reaction equation

HRID 1094970 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].N1C=CC=CC=1.[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[C:23](Cl)=[O:24]>C(Cl)Cl>[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[C:23]([NH:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5])=[O:24]

Participants

5

Reactant 3

HCID 1049PyridineHCID 8635Methyl Anthranilate2×HCID 77070Veratroyl chloride2×

Product 1

HCID 835412HCID 835412, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 2-aminobenzoate (compound A) (2.0 g) was dissolved in anhydrous methylene chloride (40.0 ml). Subsequently, pyridine (2.0 ml) and 3,4-dimethoxybenzoyl chloride (compound B) (3.14 g) were added to the solution at room temperature, and the mixture was stirred at that temperature for 30 min. After the completion of the reaction, distilled water was added thereto, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with a saturated aqueous sodium chloride solution, was dried over sodium sulfate, and was then concentrated to give methyl 2-[(3,4-dimethoxybenzoyl)amino]benzoate as a useful intermediate (4.17 g, yield 100%).

Workup

  1. customAfter the completion of the reaction
  2. distillationdistilled water
  3. additionwas added
  4. extractionthe mixture was subjected to separatory extraction with chloroform
  5. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  6. dry with materialwas dried over sodium sulfate
  7. concentrationwas then concentrated

Sources & evidence

ORD record
ord-33bbed43589b47e78e85dc326d039089
Source dataset
uspto-grants-2012_03
Patent number
US08134015B2

Reaction notes

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