Picolinic acid → Methyl 2-fluoro-4-[(pyridine-2-carbonyl)amino]benzoate

HRID 1671662Notes

Reaction equation

HRID 1671662 reaction equation
Cl.CN(C)CCCN=C=NCC.[NH2:13][C:14]1[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[C:16]([F:24])[CH:15]=1.[N:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:31](O)=[O:32]>N1C=CC=CC=1>[F:24][C:16]1[CH:15]=[C:14]([NH:13][C:31]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][N:25]=2)=[O:32])[CH:23]=[CH:22][C:17]=1[C:18]([O:20][CH3:21])=[O:19]

Participants

5

Reactant 3

HCID 1018Picolinic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21957875Methyl 4-amino-2-fluorobenzoate

Product 1

HCID 57433539Methyl 2-fluoro-4-[(pyridine-2-carbonyl)amino]benzoate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride was added to a pyridine (500 ml) solution of methyl 4-amino-2-fluorobenzoate (18.9 g) and picolinic acid (16.5 g), and stirred at room temperature for 2 hours. The solvent was evaporated away under reduced pressure, ethyl acetate (600 ml) was added to it, and the organic layer was washed with aqueous 0.25 N hydrochloric acid solution, aqueous 0.25 N sodium hydroxide solution and saturated saline water. After dried, this was concentrated under reduced pressure, and solidified from a mixed solvent of hexane/ethyl acetate, and taken out through filtration. After dried under reduced pressure, the entitled compound was obtained as a white solid.

Workup

  1. customThe solvent was evaporated away under reduced pressure, ethyl acetate (600 ml)
  2. additionwas added to it
  3. washthe organic layer was washed with aqueous 0.25 N hydrochloric acid solution, aqueous 0.25 N sodium hydroxide solution and saturated saline water
  4. customAfter dried
  5. concentrationthis was concentrated under reduced pressure
  6. filtrationtaken out through filtration
  7. customAfter dried under reduced pressure
  8. customthe entitled compound was obtained as a white solid

Sources & evidence

ORD record
ord-73cd3c2da3e34ea69f51d6a4be31fd2b
Source dataset
uspto-grants-2011_08
Patent number
US07994331B2

Reaction notes

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