Dimethylformamide → 2-Amino-5-iodo-3-methylbenzoic Acid

HRID 2427037Notes

Reaction equation

HRID 2427037 reaction equation
[NH2:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].CN(C)C=O.[I:17]N1C(=O)CCC1=O>O>[NH2:1][C:2]1[C:10]([CH3:11])=[CH:9][C:8]([I:17])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 781012-Amino-3-methylbenzoic acidHCID 120273N-Iodosuccinimide

Product 1

HCID 112312332-Amino-5-iodo-3-methylbenzoic AcidYield 60%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 2.6 g of 2-amino-3-methylbenzoic acid and 100 ml of N,N-dimethylformamide was added 2.3 g of N-iodosuccinimide at room temperature, and the mixture was stirred at room temperature for 10 hours. After water was poured to the reaction mixture, a deposited precipitate was collected by filtration to obtain 1.7 g of 2-amino-5-iodo-3-methylbenzoic acid of the formula:

Workup

  1. filtrationa deposited precipitate was collected by filtration

Sources & evidence

ORD record
ord-5a72382bd1f94e14b40049f20d4a1f37
Source dataset
uspto-grants-2011_06
Patent number
US07968573B2

Reaction notes

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