Lithium Hydroxide → 4-Amino-3-iodobenzoic Acid

HRID 854098

Reaction equation

HRID 854098 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[CH:4][C:3]=1[I:12].[OH-].[Li+]>O1CCOCC1.O>[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[I:12]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 4104649Methyl 4-amino-3-iodobenzoate

Product 1

HCID 164614-Amino-3-iodobenzoic AcidYield 98.6%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

A solution of 3.00 g (10.8 mmol) of methyl 4-amino-3-iodobenzoate and 1.30 g (54.1 mmol) of lithium hydroxide in 150 ml of a dioxane/water mixture (1:1) was stirred at room temperature for 6 h. The dioxane was distilled off in vacuo, and the remaining aqueous phase was adjusted to pH 5 with 1 M hydrochloric acid. The precipitate was filtered off with suction and washed with water. 2.80 g (98%) of the title compound were obtained as a solid.

Workup

  1. distillationThe dioxane was distilled off in vacuo
  2. filtrationThe precipitate was filtered off with suction
  3. washwashed with water

Sources & evidence

ORD record
ord-f66deb25d8444913ab070ad0765ffe80
Source dataset
uspto-grants-2007_08
Patent number
US07256288B2

Linked notes

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