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

HRID 259669

Reaction equation

HRID 259669 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-89b5131461cb4552905ee45876d6a515
Source dataset
uspto-grants-1996_06
Patent number
US05523278

Linked notes

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