Hydrochloric Acid → 2-Iodo-5-methylbenzoic acid

HRID 866589Notes

Reaction equation

HRID 866589 reaction equation
[CH3:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5](N)=[CH:4][CH:3]=1.Cl.N([O-])=O.[Na+].[I-:17].[K+].S([O-])([O-])(=O)=S.[Na+].[Na+]>O>[I:17][C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:10][C:6]=1[C:7]([OH:9])=[O:8]

Participants

7

Reactant 5

HCID 313Hydrochloric Acid2×HCID 4875Potassium IodideHCID 24477Sodium ThiosulfateHCID 762552-Amino-5-methylbenzoic acidHCID 23668193Sodium Nitrite

Product 1

HCID 1429412-Iodo-5-methylbenzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

20 G. of 5-methyl-anthranilic acid are suspended in 200 ml. of 3-N hydrochloric acid at 0° C. A solution of 10 g. of sodium nitrite and 20 ml. of water is added dropwise thereto with stirring and the mixture is further stirred for 25 minutes at 0° C. A solution of 26.5 g. of potassium iodide, 30 ml. of 3-N hydrochloric acid and 30 ml. of water is then added dropwise at 5°-10° C. The mixture is stirred for an additional 30 minutes at room temperature and for 2 hours at reflux. The mixture is cooled and sodium thiosulfate is added until the solution is yellow (5 g.). The crystalline 2-iodo-5-methyl-benzoic acid obtained is removed by filtration under vacuum and washed neutral with water. The crude acid is dissolved in ether, washed well with sodium thiosulfate solution and water, dried over sodium sulfate and evaporated, and there are obtained light-brown crystals having a melting point of 100°-112° C.

Workup

  1. customat 0° C
  2. stirringthe mixture is further stirred for 25 minutes at 0° C
  3. stirringThe mixture is stirred for an additional 30 minutes at room temperature and for 2 hours
  4. temperatureat reflux
  5. temperatureThe mixture is cooled

Sources & evidence

ORD record
ord-d37962cbeded487d8225d8cd73f92376
Source dataset
uspto-grants-1978_07
Patent number
US04100173

Reaction notes

Loading…