Methyl 2-chloronicotinate → Methyl 2-[[4-(2-methyl-1-oxopropyl)phenyl]amino]-3-pyridinecarboxylate

HRID 1271318Notes

Reaction equation

HRID 1271318 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:12])[CH:9]([CH3:11])[CH3:10])=[CH:4][CH:3]=1.Cl[C:14]1[C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=[CH:16][N:15]=1>COCCO.O>[CH3:11][CH:9]([CH3:10])[C:8]([C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:14]2[C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=[CH:16][N:15]=2)=[CH:7][CH:6]=1)=[O:12]

Participants

5

Reactant 2

HCID 819931Methyl 2-chloronicotinateHCID 51510441-(4-Aminophenyl)-2-methylpropan-1-one

Product 1

HCID 22603050Methyl 2-[[4-(2-methyl-1-oxopropyl)phenyl]amino]-3-pyridinecarboxylateYield 118.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80192-MethoxyethanolSolvent

Procedure

A mixture of 1-(4-aminophenyl)-2-methyl-1-propanone (0.0637 mol) and methyl 2-chloro-3-pyridinecarboxylate (0.0637 mol) in 2-methoxyethanol (200 ml) was stirred and refluxed for 90 hours. The mixture was taken up in water and EtOAc and extracted with EtOAc. The organic layer was separated, dried, filtered and the solvent was evaporated, yielding 22.6 g of methyl 2-[[4-(2-methyl-1-oxopropyl)phenyl]amino]-3-pyridinecarboxylate (interm. 20).

Workup

  1. temperaturerefluxed for 90 hours
  2. extractionEtOAc and extracted with EtOAc
  3. customThe organic layer was separated
  4. customdried
  5. filtrationfiltered
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-71732c7497d140babc61853ec49c0d5a
Source dataset
uspto-grants-2007_04
Patent number
US07205312B2

Reaction notes

Loading…