Water → Ethyl 4-amino-3-iodobenzoate

HRID 1264987Notes

Reaction equation

HRID 1264987 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[I:13]N1C(=O)CCC1=O.O>CN(C=O)C>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][C:12]=1[I:13]

Participants

5

Reactant 3

HCID 962WaterHCID 2337BenzocaineHCID 120273N-Iodosuccinimide

Product 1

HCID 459320Ethyl 4-amino-3-iodobenzoateYield 90.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of ethyl 4-aminobenzoate (13.0 g) in DMF (33 mL) is added a solution of N-iodosuccinimide (18.6 g) in DMF (39 mL). The reaction is stirred at room temperature overnight. The mixture is poured into 800 mL water. The resulting solid is collected and dried to yield 20.7 g (90%) of the titled compound.

Workup

  1. customThe resulting solid is collected
  2. customdried

Sources & evidence

ORD record
ord-ccd50fceb75c41f786232ebe20ae07e0
Source dataset
uspto-grants-2003_04
Patent number
US06544990B2

Reaction notes

Loading…