Diisopropyl Ether → 4-Chloro-5-(3-aminopropoxy)-7-iodoisoindolinone hydrochloride

HRID 21323Notes

Reaction equation

HRID 21323 reaction equation
[Cl:1][C:2]1[C:10]([O:11][CH2:12][CH2:13][CH2:14][NH:15]C(OC(C)(C)C)=O)=[CH:9][C:8]([I:23])=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:24].Cl.CO.C(OC(C)C)(C)C>CO>[ClH:1].[Cl:1][C:2]1[C:10]([O:11][CH2:12][CH2:13][CH2:14][NH2:15])=[CH:9][C:8]([I:23])=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:24]

Participants

5

Reactant 3

HCID 7914Diisopropyl EtherHCID 21893726Hydrochloride methanolHCID 68489177Carbamic acid,[3-[(4-chloro-2,3-dihydro-7-iodo-1-oxo-1h-isoindol-5-yl)oxy]propyl]-,1,1-dimethylethyl ester

Product 1

HCID 684884094-Chloro-5-(3-aminopropoxy)-7-iodoisoindolinone hydrochlorideYield 193%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

4-Chloro-5-[3-(tert-butoxycarbonylamino)propoxy]-7-iodoisoindolinone (101 mg, 0.216 mmol) was suspended in methanol (1.5 mL), and the suspension was added with 10% hydrogen chloride-methanol solution (1.5 mL), followed by stirring at 60° C. for 1.0 hour. The reaction mixture was added with diisopropylether. The obtained solid was collected by filtration and washed with diisopropylether, followed by drying under reduced pressure to obtain 4-chloro-5-(3-aminopropoxy)-7-iodoisoindolinone hydrochloride (84.0 mg, yield 96%).

Workup

  1. filtrationThe obtained solid was collected by filtration
  2. washwashed with diisopropylether
  3. customby drying under reduced pressure

Sources & evidence

ORD record
ord-59d850f02eb147a4a9f8d896a69cdd5b
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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