Dimethylformamide → 2-Amino-4-bromo-5-iodo-3-methoxy-6-methylbenzoic Acid

HRID 17263Notes

Reaction equation

HRID 17263 reaction equation
[I:1]N1C(=O)CCC1=O.CN(C)C=O.[NH2:14][C:15]1[C:23]([O:24][CH3:25])=[C:22]([Br:26])[CH:21]=[C:20]([CH3:27])[C:16]=1[C:17]([OH:19])=[O:18].[OH-].[Na+]>[Cl-].[Na+].O.O>[NH2:14][C:15]1[C:23]([O:24][CH3:25])=[C:22]([Br:26])[C:21]([I:1])=[C:20]([CH3:27])[C:16]=1[C:17]([OH:19])=[O:18]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 120273N-IodosuccinimideHCID 86097473HCID 86097473, compound

Product 1

HCID 860974752-Amino-4-bromo-5-iodo-3-methoxy-6-methylbenzoic AcidYield 57.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

N-Iodosuccinimide (104 mg, 461 μmol) was put into an N,N-dimethylformamide (2.0 ml) solution of 2-amino-4-bromo-3-methoxy-6-methylbenzoic acid (I-3) (100 mg, 384 μmol), followed by stirring at room temperature for 40 minutes. The reaction liquid was put into water (30 ml), followed by controlling at pH of 4 with aqueous 2 N sodium hydroxide solution, then saturated brine (30 ml) was added, the product was extracted with ethyl acetate (50 ml×2). The organic layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, the residue was purified by silica gel column chromatography (chloroform:methanol=1:0→100:3) to obtain the entitled compound (84.9 mg, 57%) as a yellow white solid.

Workup

  1. customThe reaction liquid
  2. extractionthe product was extracted with ethyl acetate (50 ml×2)
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (chloroform:methanol=1:0→100:3)

Sources & evidence

ORD record
ord-afd5140c85ea4a31a0e08235d8bf7f72
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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