Methyl 3-amino-4-methylbenzoate → HCID 58861443, compound

HRID 2109312Notes

Reaction equation

HRID 2109312 reaction equation
Br.Br[CH2:3][C:4]([C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)=[O:5].[CH3:12][O:13][C:14](=[O:23])[C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([NH2:22])[CH:16]=1.C([O-])(O)=O.[Na+]>CCO>[CH3:12][O:13][C:14](=[O:23])[C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([NH:22][CH2:3][C:4](=[O:5])[C:6]2[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=2)[CH:16]=1

Participants

5

Reactant 3

HCID 337778Methyl 3-amino-4-methylbenzoateHCID 516892Sodium BicarbonateHCID 27762343-(2-Bromoacetyl)pyridine hydrobromide

Product 1

HCID 58861443HCID 58861443, compoundYield 16.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-bromo-1-pyridin-3-yl-ethanone hydrobromide (Barlin, G. B. et al. Australian J. Chem, 1989, 1735) (500 mg, 1.78 mmol) in 2 ml of EtOH was added 3-amino-4-methyl-benzoic acid methyl ester (Lancaster; 294 mg, 1.78 mmol) and NaHCO3 (750 mg, 8.9 mmol), and the mixture was stirred for 2 h. The mixture was then filtered and washded with MeOH, then the filtrated was concentrated to a small volume and dissolved in EtOAc. The EtOAc slurry was washed with water and brine, and the washes were extracted once more with EtOAc. The combined organic portions were dried with Na2SO4, filtered, concentrated, and chromatographed (0-5% MeOH in dichloromethane) to provide 84.5 mg of 4-methyl-3-(2-oxo-2-pyridin-3-yl-ethylamino)-benzoic acid methyl ester.

Workup

  1. filtrationThe mixture was then filtered
  2. concentrationthe filtrated was concentrated to a small volume
  3. dissolutiondissolved in EtOAc
  4. washThe EtOAc slurry was washed with water and brine
  5. extractionthe washes were extracted once more with EtOAc
  6. dry with materialThe combined organic portions were dried with Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customchromatographed (0-5% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-9b7b08664e184237b3e77bbe88d39cdb
Source dataset
uspto-grants-2009_04
Patent number
US07514458B2

Reaction notes

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