Hydrochloric Acid → 4-chloro-N,2-dihydroxybenzamide

HRID 375063Notes

Reaction equation

HRID 375063 reaction equation
Cl.[NH2:2][OH:3].C[O-].[Na+].[Cl:7][C:8]1[CH:9]=[C:10]([OH:18])[C:11](=[CH:16][CH:17]=1)[C:12](OC)=[O:13].Cl>CO>[Cl:7][C:8]1[CH:9]=[C:10]([OH:18])[C:11](=[CH:16][CH:17]=1)[C:12]([NH:2][OH:3])=[O:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 327085Methyl 4-chloro-2-hydroxybenzoateHCID 443297Hydroxyamine hydrochlorideHCID 10942334Sodium Methoxide

Product 1

HCID 27818484-chloro-N,2-dihydroxybenzamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Hydroxylamine hydrochloride (20.65 g, 0.297 mol) is added to a mixture of sodium methoxide (53 g, 0.99 mol) in methanol while maintaining the temperature below 10° C. A mixture of methyl 4-chlorosalicylate (46.2 g, 0.248 mol) in methanol is then added to the reaction mixture and the resultant mixture is stirred at room temperature for 10 days, acidified with concentrated hydrochloric acid (pH3) and filtered to give the title product as an off-white solid which is identified by NMR spectral analyses.

Workup

  1. temperaturewhile maintaining the temperature below 10° C
  2. additionis then added to the reaction mixture
  3. filtrationfiltered

Sources & evidence

ORD record
ord-801d2079e4b3482bb1c0a6b6c972a329
Source dataset
uspto-grants-1996_01
Patent number
US05484763

Reaction notes

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