Pyridine → 4-(2-Bromo-propionylamino)-benzoic acid methyl ester

HRID 526686Notes

Reaction equation

HRID 526686 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][CH:5]=1.N1C=CC=CC=1.[Br:18][CH:19]([CH3:23])[C:20](Br)=[O:21]>C1(C)C=CC=CC=1.O>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:20](=[O:21])[CH:19]([Br:18])[CH3:23])=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 12082Methyl 4-aminobenzoateHCID 79047Propanoyl bromide, 2-bromo-

Product 1

HCID 899078694-(2-Bromo-propionylamino)-benzoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a solution of 1.1 g of 4-Amino-benzoic acid methyl ester in 17 ml of toluene were added 2.2 ml of pyridine and 1.5 g of 2-Bromo-propionyl bromide at room temperature. After 16 h the reaction mixture was diluted with water and filtered through a chem Elut® cartridge by eluting with ethyl acetate. The solvents were removed under reduced pressure and the crude product was purified by chromatography on silica gel eluting with a gradient of n-heptane/ethyl acetate. The fractions containing the product were combined and the solvent evaporated under reduced pressure. Yield: 2 g.

Workup

  1. filtrationfiltered through a chem Elut® cartridge
  2. washby eluting with ethyl acetate
  3. customThe solvents were removed under reduced pressure
  4. customthe crude product was purified by chromatography on silica gel eluting with a gradient of n-heptane/ethyl acetate
  5. additionThe fractions containing the product
  6. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-b63e9924a8b442ad8668f01c259495a5
Source dataset
uspto-grants-2016_05
Patent number
US09346757B2

Reaction notes

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