Pyridine → 4-[(6-Chloro-pyridine-3-carbonyl)-amino]-3-hydroxy-benzoic acid

HRID 2196478Notes

Reaction equation

HRID 2196478 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[OH:11].N1C=CC=CC=1.[Cl:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][N:20]=1>C1COCC1>[Cl:18][C:19]1[N:20]=[CH:21][C:22]([C:23]([NH:1][C:2]2[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=2[OH:11])=[O:24])=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 1375664-Amino-3-hydroxybenzoic acidHCID 27821656-Chloronicotinoyl Chloride

Product 1

HCID 582308724-[(6-Chloro-pyridine-3-carbonyl)-amino]-3-hydroxy-benzoic acidYield 85.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4-Amino-3-hydroxy benzoic acid (0.490 g, 0.0032 mols) and pyridine (0.76 g, 0.0096 mols) in 50 ml dry THF is added 6-chloronicotinoyl chloride (0.56 g, 0.0032 mols) and the solution is stirred under nitrogen atmosphere at RT for 10 hrs and then refluxed for 3 hrs. The reaction mixture is rotary evaporated and the residue is slurried in water and filtered to get the amide (0.8 g) which is taken for the next step without further purification.

Workup

  1. temperaturerefluxed for 3 hrs
  2. customThe reaction mixture is rotary evaporated
  3. filtrationfiltered

Sources & evidence

ORD record
ord-cdcffe8cfe834ad0b105bc19679dec60
Source dataset
uspto-grants-2012_12
Patent number
US08338459B2

Reaction notes

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