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

HRID 902762

Reaction equation

HRID 902762 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 68.6%

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 (128 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-0296863cb5b848208ac8a77cd8b340c4
Source dataset
uspto-grants-2008_04
Patent number
US07365225B2

Linked notes

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