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

HRID 1986425Notes

Reaction equation

HRID 1986425 reaction equation
[OH:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]([NH2:11])=[CH:4][CH:3]=1.C(=O)([O-])O.[Na+].Cl[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19].Cl>C(OCC)C.O>[CH2:21]([O:20][C:18]([NH:11][C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[CH:10][C:6]=1[C:7]([OH:9])=[O:8])=[O:19])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10387Benzyl chloroformateHCID 1645925-Hydroxyanthranilic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 183153542-(((Benzyloxy)carbonyl)amino)-5-hydroxybenzoic acidYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a mixture of 5-hydroxyanthranilic acid (50 g, 0.33 mol), sodium hydrogen carbonate (109 g, 1.3 mol) and water (200 ml) was added dropwise a solution of benzyl chloroformate (52 ml, 0.36 mol) in diethyl ether (200 ml) with stirring, and the mixture was stirred at room temperature for 3 hrs. The reaction mixture was acidified by adding conc. hydrochloric acid and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated and the obtained crystals were washed with diisopropyl ether and hexane to give 2-{[(benzyloxy)carbonyl]amino}-5-hydroxybenzoic acid (91.6 g, yield 98%) as brown crystals.

Workup

  1. stirringthe mixture was stirred at room temperature for 3 hrs
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. washthe obtained crystals were washed with diisopropyl ether and hexane

Sources & evidence

ORD record
ord-b9ac554951a24f39825bdee3caa7d573
Source dataset
uspto-grants-2009_06
Patent number
US07547710B2

Reaction notes

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