3-Hydroxyanthranilic Acid → HCID 66621334, compound

HRID 415200Notes

Reaction equation

HRID 415200 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([OH:7])=[O:6])[C:3]=1[NH2:11].N1C=CC=CC=1.[C:18](Cl)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[N:21][CH:20]=1>C1(C)C=CC=CC=1>[OH:1][C:2]1[C:3]([NH:11][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[N:21][CH:20]=2)=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 863-Hydroxyanthranilic AcidHCID 1049PyridineHCID 82604Nicotinoyl chloride

Product 1

HCID 66621334HCID 66621334, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Thionyl chloride (10 mL) was added to nicotinic acid (370 mg, 3 mmol) and the mixture was stirred at reflux for 6 hr. Thionyl chloride was evaporated under reduced pressure and the residues was dried in vacuum to obtain nicotinoyl chloride. 3-Hydroxyanthranilic acid (153 mg, 1.0 mmol) and pyridine (240 mg, 3.0 mmol) were added to toluene (10 mL) and the mixture was stirred at room temperature for 30 min. Then nicotinoyl chloride (420 mg, 3.0 mmol) was added. The mixture was stirred at room temperature for 30 min and then at 80° C. for 2 hr. The resulting mixture was extracted with ethyl acetate (100 mL×4) and concentrated. The crude product was purified by column chromatography (silica gel, petroleum ether:ethyl acetate 20: to 5:1) to get 3-hydroxy-2-(nicotinamido)benzoic acid as a solid (210 mg, yield 81%). LC-MS (ESI) m/z 259 [M+1]+.

Workup

  1. stirringThe mixture was stirred at room temperature for 30 min
  2. waitat 80° C. for 2 hr
  3. extractionThe resulting mixture was extracted with ethyl acetate (100 mL×4)
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatography (silica gel, petroleum ether:ethyl acetate 20: to 5:1)

Sources & evidence

ORD record
ord-4716f13850844710bb1b1010ab11fe46
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

Loading…