Anthranilic Acid → 2-(Octanoylamino)benzoic acid

HRID 36312

Reaction equation

HRID 36312 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].N1C=[CH:15][CH:14]=[CH:13][CH:12]=1.[Cl-].Cl.[O:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1>>[C:20]([NH:4][C:3]1[C:2](=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:1]([OH:10])=[O:9])(=[O:19])[CH2:21][CH2:22][CH2:23][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

6

Reactant 5

HCID 227Anthranilic AcidHCID 312ChlorideHCID 313Hydrochloric AcidHCID 1049PyridineHCID 8028Tetrahydrofuran2×

Product 1

HCID 41572202-(Octanoylamino)benzoic acidYield 79.4%

Procedure

Anthranilic acid was dissolved in a mixed solvent containing pyridine and tetrahydrofuran (THF) in 5:5 ratio and a THF solution of n-caprioyl chloride was dropped to the solution during several hours for reaction. After the reaction, hydrochloric acid was added to the reaction mixture. Pyridine hydrochloride was filtered and the solvent was removed. N-n-octanoylanthranilic acid was obtained from the remaining reactant after the purification by column chromatography with the yield of 79.4%.

Workup

  1. additionwas added to the reaction mixture
  2. filtrationPyridine hydrochloride was filtered
  3. customthe solvent was removed

Sources & evidence

ORD record
ord-26de8cb6b8ab4be3a4b1393e37538166
Source dataset
uspto-grants-1995_05
Patent number
US05413794

Linked notes

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