5-Chlorosalicylic Acid → HCID 929387, compound

HRID 983790Notes

Reaction equation

HRID 983790 reaction equation
[H][H].[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([OH:13])=[C:8]([CH:12]=1)[C:9]([OH:11])=[O:10].[I:14]N1C(=O)CCC1=O>C(O)(=O)C>[Cl:3][C:4]1[CH:5]=[C:6]([I:14])[C:7]([OH:13])=[C:8]([CH:12]=1)[C:9]([OH:11])=[O:10]

Participants

5

Reactant 3

HCID 94475-Chlorosalicylic AcidHCID 120273N-Iodosuccinimide2×HCID 178418361HCID 178418361, compound

Product 1

HCID 929387HCID 929387, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

For example, a mixture of a compound of formula 40 wherein R3 and R4 are hydrogen and R5 is chloro, i.e., 5-chloro-2-hydroxy benzoic acid, (5.0 g, 29 mmol) and N-iodosuccinimide (7.17 g, 32 mmol) in acetic acid (30 mL) was heated to 95° C. for 2 h. Additional N-iodosuccinimide (0.70 g, 3.1 mmol) was added and heating was continued for 1 h. The mixture was cooled and poured over ice. The precipitate was isolated by filtration and the crude material was purified by recrystallization from methanol/water. The solid was isolated by filtration, rinsed with water and dried. 5-Chloro-2-hydroxy-3-iodo-benzoic acid 41 was obtained as a tan crystalline solid (6.14 g, 71% yield).

Workup

  1. temperatureheating
  2. temperatureThe mixture was cooled
  3. additionpoured over ice
  4. customThe precipitate was isolated by filtration
  5. customthe crude material was purified by recrystallization from methanol/water
  6. customThe solid was isolated by filtration
  7. washrinsed with water
  8. customdried

Sources & evidence

ORD record
ord-093588158f1a480cb2455fe4b72ca58d
Source dataset
uspto-grants-2005_03
Patent number
US06867200B1

Reaction notes

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