Water → 2-Iodo-4-nitroaniline

HRID 1732866Notes

Reaction equation

HRID 1732866 reaction equation
[I:1]Cl.[N+:3]([C:6]1[CH:12]=[CH:11][C:9]([NH2:10])=[CH:8][CH:7]=1)([O-:5])=[O:4].O>C(O)(=O)C>[I:1][C:11]1[CH:12]=[C:6]([N+:3]([O-:5])=[O:4])[CH:7]=[CH:8][C:9]=1[NH2:10]

Participants

5

Reactant 3

HCID 962WaterHCID 74754-NitroanilineHCID 24640Iodine chloride

Product 1

HCID 2226292-Iodo-4-nitroanilineYield 107.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of iodine monochloride (23.54 g) in acetic acid (50 ml) is added dropwise over an hour to a stirred solution of p-nitroaniline (20 g). After stirring for another hour, the dark mixture is poured into water (1 liter), the precipitated yellow solid is collected and dried to afford 41.15 g title product, m.p. 90°-95° C.

Workup

  1. customthe precipitated yellow solid is collected
  2. customdried

Sources & evidence

ORD record
ord-6d705820f62e49a793492c17e7ed4fb4
Source dataset
uspto-grants-1980_12
Patent number
US04239708

Reaction notes

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