Hydrochloric Acid → N,2-Dihydroxy-4-iodobenzamide

HRID 428229Notes

Reaction equation

HRID 428229 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([I:12])[CH:9]=[CH:8][C:3]=1[C:4](OC)=[O:5].Cl.[NH2:14][OH:15].Cl>[OH-].[Na+]>[OH:15][NH:14][C:4](=[O:5])[C:3]1[CH:8]=[CH:9][C:10]([I:12])=[CH:11][C:2]=1[OH:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 443297Hydroxyamine hydrochlorideHCID 11380407Methyl 4-iodosalicylate

Product 1

HCID 18357907N,2-Dihydroxy-4-iodobenzamide

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

23.3 g (84 mmol) of methyl 2-hydroxy-4-iodobenzoate and 360 ml of sodium hydroxide solution (1 N) are introduced into a three-necked flask under a stream of nitrogen. 8 g (113 mmol) of hydroxylamine hydrochloride are added and the mixture is stirred at room temperature for two hours. The reaction medium is adjusted to pH 7-8 with concentrated hydrochloric acid and the solid is filtered off. The solid is dissolved in ethyl acetate and washed with water, and the organic phase is separated out after settling has taken place, dried over magnesium sulphate and evaporated. The residue is triturated from heptane, filtered and dried. 17.6 g (71.5%) of the expected product are collected, with a melting point of 195-6° C.

Workup

  1. filtrationthe solid is filtered off
  2. dissolutionThe solid is dissolved in ethyl acetate
  3. washwashed with water
  4. customthe organic phase is separated out after settling
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. customThe residue is triturated from heptane
  8. filtrationfiltered
  9. customdried
  10. custom17.6 g (71.5%) of the expected product are collected, with a melting point of 195-6° C.

Sources & evidence

ORD record
ord-181262a53bed48bc836e25305db4dee8
Source dataset
uspto-grants-2001_11
Patent number
US06313162B1

Reaction notes

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