Hydrochloric Acid → 4-{[(Benzyloxy)carbonyl]amino}-2-hydroxybenzoic acid

HRID 733503

Reaction equation

HRID 733503 reaction equation
[Na].[NH2:2][C:3]1[CH:4]=[C:5]([OH:12])[C:6](=[CH:10][CH:11]=1)[C:7]([O-:9])=[O:8].Cl[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15].Cl>[OH-].[Na+]>[CH2:17]([O:16][C:14]([NH:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[C:5]([OH:12])[CH:4]=1)=[O:15])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10387Benzyl chloroformateHCID 178507646HCID 178507646, compound

Product 1

HCID 2460304-{[(Benzyloxy)carbonyl]amino}-2-hydroxybenzoic acidYield 69.1%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

To a solution of sodium-p-aminosalicylate (100 g, 0.65 mol) in 10% aqueous NaOH solution (1 L) was added a 50% wt solution of benzyl chloroformate (670 g, 1.96 mol in toluene) at 0° C. and stirred at rt for 48 h. The reaction mixture was cooled and acidified with a 10% aqueous HCl at 0° C. The solid obtained was filtered and washed with cold water and dried. The solid was treated with PetEther and filtered to give the title compound (129 g, 68%) used in the next steps without further purification.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customThe solid obtained
  3. filtrationwas filtered
  4. washwashed with cold water
  5. customdried
  6. additionThe solid was treated with PetEther
  7. filtrationfiltered

Sources & evidence

ORD record
ord-8781117e63c04513a618de00140ecccb
Source dataset
uspto-grants-2009_09
Patent number
US07589232B2

Linked notes

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