Pyridine → 4-[(3-Chloro-1-oxopropyl)amino]-2-hydroxybenzoic acid

HRID 487834Notes

Reaction equation

HRID 487834 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:11])[C:5](=[CH:9][CH:10]=1)[C:6]([OH:8])=[O:7].[Cl:12][CH2:13][CH2:14][C:15](Cl)=[O:16].N1C=CC=CC=1>C(#N)C>[Cl:12][CH2:13][CH2:14][C:15]([NH:1][C:2]1[CH:3]=[C:4]([OH:11])[C:5](=[CH:9][CH:10]=1)[C:6]([OH:8])=[O:7])=[O:16]

Participants

5

Reactant 3

HCID 1049PyridineHCID 46494-Aminosalicylic AcidHCID 693643-Chloropropionyl chloride

Product 1

HCID 1317183674-[(3-Chloro-1-oxopropyl)amino]-2-hydroxybenzoic acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

7.5 g of 4-Aminosalicyclic acid was dissolved in 300 ml of acetonitrile at about 60° C. 12 ml of 3-chloropropionyl chloride was added dropwise and followed by addition of 5 ml of pyridine, the resulting mixture was refluxed for three hours. The mixture, which became clear after approximately 20 minutes of refluxing, was cooled and evaporated to dryness under reduced pressure. A gummy oil was dissolved in isopropanol-water and refrigerated for several days. A small amount of solid thus produced was filtered off. The filtrate was evaporated to dryness and approximately 16.8 g of crude 4-(3-chloropropionamido) salicyclic acid was produced. A lens treated with this compound was found to be clear with excellent UV blockage up to about 320 nm.

Workup

  1. temperaturethe resulting mixture was refluxed for three hours
  2. temperatureof refluxing
  3. temperaturewas cooled
  4. customevaporated to dryness under reduced pressure
  5. dissolutionA gummy oil was dissolved in isopropanol-water
  6. waitrefrigerated for several days
  7. customA small amount of solid thus produced
  8. filtrationwas filtered off
  9. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-a67fd52bda2a462dbf1b94fadfca8767
Source dataset
uspto-grants-1994_03
Patent number
US05298033

Reaction notes

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