Hydrochloric Acid → HCID 21520617, compound

HRID 1282940Notes

Reaction equation

HRID 1282940 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([NH2:11])[CH:8]=[C:4]([C:5]([OH:7])=[O:6])[C:3]=1[OH:12].N1C=CC=CC=1.C([O:22][C:23]1[C:24](=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:25](Cl)=[O:26])(=O)C.Cl>CC(C)=O.CO.[OH-].[Na+]>[Br:1][C:2]1[CH:10]=[C:9]([CH:8]=[C:4]([C:5]([OH:7])=[O:6])[C:3]=1[OH:12])[NH:11][C:25](=[O:26])[C:24]1[CH:28]=[CH:29][CH:30]=[CH:31][C:23]=1[OH:22]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 796682-Acetoxybenzoyl chlorideHCID 2032755554669-99-7

Product 1

HCID 21520617HCID 21520617, compoundYield 95.8%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolvent2×HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

3-Bromo-5-aminosalicylic acid (0.73 g.) was dissolved in acetone (30 ml.) and pyridine (0.4 ml.) to which an acetone (14 ml.) solution containing acetyl-salicyloyl chloride (prepared from 0.53 g. of acetyl-salicylic acid) was added dropwise with stirring. After reaction the solution was evaporated to dryness under reduced and the residue was dissolved in ethyl acetate. After washing the solution with water and 1 N hydrochloric acid successively, the ethyl acetate was evaporated off under reduced pressure, yielding a residue which was redissolved in a mixture of methanol and 2 N sodium hydroxide (14 ml. each). After stirring the solution for several hours and then acidifying with 2 N hydrochloric acid solution, a precipitate was formed, collected and crystallized from aqueous methanol to give light brown crystals (0.90 g.) of 3'-bromo5'-carboxy-2,4'-dihydroxybenzanilide,

Workup

  1. additionwas added dropwise
  2. customAfter reaction the solution
  3. customwas evaporated to dryness
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washAfter washing the solution with water and 1 N hydrochloric acid successively
  6. customthe ethyl acetate was evaporated off under reduced pressure
  7. customyielding a residue which
  8. stirringAfter stirring the solution for several hours
  9. customa precipitate was formed
  10. customcollected
  11. customcrystallized from aqueous methanol

Sources & evidence

ORD record
ord-3c70c25002a745af95497b0d8106c6db
Source dataset
uspto-grants-1976_08
Patent number
US03973038

Reaction notes

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