Acetone → HCID 20327542, compound

HRID 2398274Notes

Reaction equation

HRID 2398274 reaction equation
[Br:1][C:2]1[CH:10]=[C:9](N)[CH:8]=[C:4]([C:5]([OH:7])=[O:6])[C:3]=1[OH:12].[N:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[C:19](OC1C(=CC=CC=1)C(Cl)=O)(=[O:21])C.Cl.C[C:34](C)=[O:35]>CO.[OH-].[Na+]>[Br:1][C:2]1[C:3]([OH:12])=[C:4]([C:5]([OH:7])=[O:6])[CH:8]=[C:9]([CH:10]=1)[C:19]([NH:13][C:18]1[CH:17]=[CH:16][CH:15]=[CH:14][C:34]=1[OH:35])=[O:21]

Participants

8

Reactant 5

HCID 180Acetone2×HCID 313Hydrochloric AcidHCID 1049PyridineHCID 796682-Acetoxybenzoyl chlorideHCID 2032755554669-99-7

Product 1

HCID 20327542HCID 20327542, compoundYield 81.1%

Reagents, catalysts & solvents 2

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 pressure 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 5-bromo-3-carboxy-2' ,4-dihydroxybenzanilide. Yield: 81.1%. Decomposition point: 275° C.

Workup

  1. additionwas added dropwise
  2. customAfter reaction the solution
  3. customwas evaporated to dryness under reduced pressure
  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-9412d672a1df469bb45119614fed1234
Source dataset
uspto-grants-1977_05
Patent number
US04024253

Reaction notes

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