Ethanol → Ethyl 5-amino-2-hydroxybenzoate

HRID 1956425Notes

Reaction equation

HRID 1956425 reaction equation
[NH2:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]([OH:11])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH2:17](O)[CH3:18]>>[NH2:1][C:2]1[CH:10]=[C:6]([C:7]([O:9][CH2:17][CH3:18])=[O:8])[C:5]([OH:11])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 40755-Aminosalicylic Acid

Product 1

HCID 13445456Ethyl 5-amino-2-hydroxybenzoate

Procedure

A mixture of 5-aminosalicylic acid (15 g), absolute ethanol (250 ml) and concentrated sulphuric acid (7.5 ml) was boiled under reflux with stirring for 8.5 hours. The reaction mixture was evaporated to dryness. Water (20 ml) was added to the residue and the mixture filtered. The filtrate was basified with saturated bicarbonate solution and the solid collected by filtration. The solid was extracted into dichloromethane and the extract evaporated to dryness. The residue was triturated with petroleum ether b.p. 40°-60° C. and filtered to give ethyl 5-aminosalicylate, m.p. 44° C.

Workup

  1. temperatureunder reflux
  2. customThe reaction mixture was evaporated to dryness
  3. additionWater (20 ml) was added to the residue
  4. filtrationthe mixture filtered
  5. filtrationthe solid collected by filtration
  6. extractionThe solid was extracted into dichloromethane
  7. customthe extract evaporated to dryness
  8. customThe residue was triturated with petroleum ether b.p. 40°-60° C.
  9. filtrationfiltered

Sources & evidence

ORD record
ord-7feac025998842659c85be094b063871
Source dataset
uspto-grants-1998_07
Patent number
US05780482

Reaction notes

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