Chloroform → 4-Hydroxy-7-iodoisoindolinone

HRID 21087Notes

Reaction equation

HRID 21087 reaction equation
COC[O:4][C:5]1[CH:13]=[CH:12][C:11]([I:14])=[C:10]2[C:6]=1[CH2:7][N:8](C(C)(C1C=CC=CC=1)C)[C:9]2=[O:15].C(Cl)(Cl)Cl>Cl.CO>[OH:4][C:5]1[CH:13]=[CH:12][C:11]([I:14])=[C:10]2[C:6]=1[CH2:7][NH:8][C:9]2=[O:15]

Participants

4

Reactant 2

HCID 6212ChloroformHCID 68490938HCID 68490938, compound

Product 1

HCID 684897404-Hydroxy-7-iodoisoindolinoneYield 85.1%

Reagents, catalysts & solvents 1

HCID 21893726Hydrochloride methanolSolvent2×

Conditions

Temperature
70 °C

Procedure

4-Methoxymethoxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone (463 mg, 1.06 mmol) was dissolved in 10% hydrogen chloride-methanol solution (14 mL), and the solution was stirred at 70° C. for 2.5 hours. Then, the solution was added with 10% hydrogen chloride-methanol solution (4.3 mL) and further stirred at 2.5 hours. The reaction mixture was added with chloroform and purified by slurry. The solid was collected by filtration and washed with chloroform/methanol (9/1). The obtained solid was dried under reduced pressure to obtain 4-hydroxy-7-iodoisoindolinone (248 mg, yield 85%).

Workup

  1. stirringfurther stirred at 2.5 hours
  2. custompurified by slurry
  3. filtrationThe solid was collected by filtration
  4. washwashed with chloroform/methanol (9/1)
  5. customThe obtained solid was dried under reduced pressure

Sources & evidence

ORD record
ord-909e71bd33ed45648f3d27ffa574164a
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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