Methyl 2-chloronicotinate → HCID 22603050, compound

HRID 2224639

Reaction equation

HRID 2224639 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 22603050HCID 22603050, compoundYield 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 2chloro-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-6d6521987d964fb5bee6b37ddd40d16e
Source dataset
uspto-grants-2008_05
Patent number
US07378433B2

Linked notes

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