Water → Ethyl 4-amino-3-iodobenzoate

HRID 2086603Notes

Reaction equation

HRID 2086603 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-319197fca15a44a69411ce866bb3f216
Source dataset
uspto-grants-2004_04
Patent number
US06727248B2

Reaction notes

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