Pyridine → HCID 68409078, compound

HRID 642107Notes

Reaction equation

HRID 642107 reaction equation
N[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.Cl[C:13](=[O:18])[C:14]([O:16][CH3:17])=[O:15].[N:19]1C=CC=CC=1>>[CH3:17][O:16][C:14](=[O:15])[C:13]([NH:19][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:2]=1)[C:6]([O:8][CH3:9])=[O:7])=[O:18]

Participants

4

Reactant 3

HCID 1049PyridineHCID 12082Methyl 4-aminobenzoateHCID 79846Methyl chloroglyoxylate

Product 1

HCID 68409078HCID 68409078, compound

Procedure

To a solution of methyl 4-aminobenzoate (500 mg, 3.31 mmol) in anydrous pyridine (10 mL) was added dropwise methyl chlorooxoacetate (370 μL, 3.97 mmol) at 0° C. After 5 min the temperature was allowed to warm up to rt. After 90 min, aminomethyl resin (Polymers Laboratories PL-AMS, 1.96 mmol/g, 720 mg) was added and the resulting mixture was stirred overnight at rt. After filtration and rinsing the resin, water (50 mL) was added into the filtrate and a white solid precipated out. Filtration and washing with water gave a solid which was dried under vacuo at 70° C. for 5 hrs. The title compound (554 mg) was obtained as a white solid (71%) in 99.6% purity by HPLC (MaxPlot detection between 230 and 400 nm).

Workup

  1. waitAfter 90 min
  2. additionaminomethyl resin (Polymers Laboratories PL-AMS, 1.96 mmol/g, 720 mg) was added
  3. filtrationAfter filtration
  4. washrinsing the resin, water (50 mL)
  5. additionwas added into the filtrate
  6. filtrationFiltration
  7. washwashing with water
  8. customgave a solid which
  9. customwas dried under vacuo at 70° C. for 5 hrs

Sources & evidence

ORD record
ord-42040d4417b946f2b19f7bc689ac981f
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

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