Water → 4-Chloro-2-iodo-6-nitroaniline

HRID 326642

Reaction equation

HRID 326642 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[I:12]Cl.O>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5]([NH2:6])=[C:7]([I:12])[CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 69794-Chloro-2-nitroanilineHCID 24640Iodine chloride

Product 1

HCID 121435644-Chloro-2-iodo-6-nitroanilineYield 14.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 4-chloro-2-nitroaniline (34.5 g) in acetic acid (500 ml) was refluxed with iodine monochloride (65.0 g) for 7 h with stirring, then was cooled and added to excess water. The precipitate was filtered off, washed with aqueous sodium sulphite and after column chromatography yielded 4-chloro-2-iodo-6-nitroaniline (8.5 g). δ (360 MHz, DMSO-d6) 7.13 (2H, bs, NH2), 8.08 (1H, d, 3-H) and 8.13 (1H, d, 5-H).

Workup

  1. temperaturewas cooled
  2. filtrationThe precipitate was filtered off
  3. washwashed with aqueous sodium sulphite

Sources & evidence

ORD record
ord-dd2f7adc642445489ee6650eb1ed53a0
Source dataset
uspto-grants-1993_12
Patent number
US05270309

Linked notes

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