Hydrochloric Acid → 2-Iodo-4-methoxybenzoic acid
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](N)[C:6](=[CH:10][CH:11]=1)[C:7]([OH:9])=[O:8].Cl.N([O-])=O.[Na+].[I-:18].[K+].S(=O)(=O)(O)O>O>[I:18][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=[O:8]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
150 G. of 4-methoxy-anthranilic acid are suspended at 0° C. in 2 liters of water and 80 ml. of concentrated hydrochloric acid. A solution of 62 g. of sodium nitrite in 130 ml. of water is added dropwise thereto with stirring at 0°-5° C. over a period of 30 minutes. The resulting diazonium salt solution is stirred for an additional 15 minutes at 0°-5° C. A solution of 164 g. of potassium iodide in 700 ml. of 5-N sulfuric acid is subsequently added dropwise at 3°-6° C. over a period of 45 minutes. The entire mixture is stirred at room temperature for 30 minutes and subsequently warmed slowly to reflux temperature. After boiling at reflux temperature for 2 hours, the mixture is cooled to room temperature. The separated brown crystals are removed by filtration and washed neutral with water. The filter cake is dried under reduced pressure, and there is obtained 2-iodo-4-methoxy-benzoic acid in the form of brown crystals having a melting point of 174° C.
Workup
- stirringThe entire mixture is stirred at room temperature for 30 minutes
- temperaturesubsequently warmed slowly
- temperatureto reflux temperature
- temperatureat reflux temperature for 2 hours
- customThe separated brown crystals are removed by filtration
- washwashed neutral with water
- customThe filter cake is dried under reduced pressure
Sources & evidence
- ORD record
- ord-69ffca04d68546d5a20869910ea30a4c
- Source dataset
- uspto-grants-1976_12
- Patent number
- US03996229
Reaction notes
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