Pyridine → 205312-69-2

HRID 2042753Notes

Reaction equation

HRID 2042753 reaction equation
[NH2:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.N1C=CC=CC=1.[C:18](Cl)(=[O:21])[CH:19]=[CH2:20].C(Cl)(Cl)Cl.CO>CN(C=O)C.O>[C:18]([NH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([OH:9])=[O:8])=[CH:10][CH:11]=1)(=[O:21])[CH:19]=[CH2:20]

Participants

7

Reactant 4

HCID 1049PyridineHCID 13140Acryloyl chlorideHCID 655264-(Aminomethyl)Benzoic AcidHCID 21584188Chloroform methanol

Product 1

HCID 24707669205312-69-2Yield 10.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4-aminomethyl benzoic acid (5 g, 33.0 mmol) and pyridine (1.5 mL) in DMF (35 mL) was added acryloyl chloride (2.97 g, 33.0 mmol) at 0° C. dropwise. The reaction mixture was allowed to come to room temperature and stirred further for 4 days. After that it was poured in water (100 mL) and stirred for 15 min and then extracted with EtOAc (3×150 mL). The combined organic extract was washed with brine (50 mL), dried over Na2SO4 and concentrated under reduced pressure to give crude product. Column chromatography (silica, 230-400, mixtures of CHCl3/MeOH) provided the desired product (0.7 g, 9.95%) as a white solid which was used for next step.

Workup

  1. customto come to room temperature
  2. stirringstirred for 15 min
  3. extractionextracted with EtOAc (3×150 mL)
  4. extractionThe combined organic extract
  5. washwas washed with brine (50 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customto give crude product

Sources & evidence

ORD record
ord-5b1f18f622564a87afccfc835ecd383b
Source dataset
uspto-grants-2013_11
Patent number
US08586600B2

Reaction notes

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