Hydrochloric Acid → 2-(((Benzyloxy)carbonyl)amino)-5-hydroxybenzoic acid

HRID 275832

Reaction equation

HRID 275832 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:12](Cl)([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13].Cl>[OH-].[Na+]>[CH2:15]([O:14][C:12]([NH:1][C:2]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5])=[O:13])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10387Benzyl chloroformateHCID 1645925-Hydroxyanthranilic acid

Product 1

HCID 183153542-(((Benzyloxy)carbonyl)amino)-5-hydroxybenzoic acidYield 51.5%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

2-Amino-5-hydroxy-benzoic acid (3.0 g) was dissolved in a 1N aqueous solution of sodium hydroxide (50 ml), to which was added dropwise carbobenzyloxy chloride (3.5 g). The mixture was stirred for one hour at room temperature, which was neutralized with 1N hydrochloric acid, followed by extraction with ethyl acetate (100 ml). The organic layer was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled under reduced pressure to leave 2-benzyloxycarbonylamino-5-hydroxybenzoic acid as blackish brown crystals (2.9 g).

Workup

  1. extractionfollowed by extraction with ethyl acetate (100 ml)
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled under reduced pressure

Sources & evidence

ORD record
ord-376d0988882649fe9f625f30c1039e18
Source dataset
uspto-grants-2002_03
Patent number
US06352982B1

Linked notes

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