Triethylamine → 4-Methyl-3-(3-(pyridin-3-yl)acrylamido)benzoic acid methyl ester

HRID 1968939Notes

Reaction equation

HRID 1968939 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]=[CH:9][C:10](Cl)=[O:11])[CH:3]=1.[CH3:13][O:14][C:15](=[O:24])[C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[C:18]([NH2:23])[CH:17]=1.C(N(CC)CC)C>ClCCl>[CH3:13][O:14][C:15](=[O:24])[C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[C:18]([NH:23][C:10](=[O:11])[CH:9]=[CH:8][C:4]2[CH:3]=[N:2][CH:7]=[CH:6][CH:5]=2)[CH:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 337778Methyl 3-amino-4-methylbenzoateHCID 713600273-(3-Pyridyl)acryloyl chloride hydrochloride

Product 1

HCID 674942564-Methyl-3-(3-(pyridin-3-yl)acrylamido)benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 3-pyridin-3-ylacryloyl chloride hydrochloride (5.1 g) in anhydrous dichloromethane (100 ml), a solution of 3-amino-4-methyl benzoic acid methyl ester (2.75 g) and triethylamine (2.3 ml) in dichloromethane (50 ml) was added dropwise slowly in an ice-bath with the temperature no more than 5° C. After addition, the reaction was carried out for 30 min in an ice-bath, and to then at room temperature for 3 h. The completion of reaction was indicated by TLC. The reaction mixture was concentrated and dissolved into 150 ml of sodium hydroxide solution (10%). The reaction mixture was extracted with EtOAc (30 ml*3). The organic layer was dried over anhydrous MgSO4, and filtered. Most EtOAc was removed by evaporation under reduced pressure. The is residue was cooled in refrigerator. Crystallization and filtration provided a light yellow crystal.

Workup

  1. additionAfter addition
  2. waitto then at room temperature for 3 h
  3. customThe completion of reaction
  4. concentrationThe reaction mixture was concentrated
  5. dissolutiondissolved into 150 ml of sodium hydroxide solution (10%)
  6. extractionThe reaction mixture was extracted with EtOAc (30 ml*3)
  7. dry with materialThe organic layer was dried over anhydrous MgSO4
  8. filtrationfiltered
  9. customMost EtOAc was removed by evaporation under reduced pressure
  10. temperatureThe is residue was cooled in refrigerator
  11. customCrystallization and filtration
  12. customprovided a light yellow crystal

Sources & evidence

ORD record
ord-3aa95ec22ce9466faf9747af9c4c89e2
Source dataset
uspto-grants-2013_04
Patent number
US08426446B2

Reaction notes

Loading…