Hydrochloride methanol → HCID 86628295, compound

HRID 21262Notes

Reaction equation

HRID 21262 reaction equation
COC[O:4][C:5]1[C:13]([CH:14](OC)[O:15]C)=[CH:12][C:11]([I:19])=[C:10]2[C:6]=1[CH:7]([OH:30])[N:8]([C:21]([CH3:29])([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH3:22])[C:9]2=[O:20].Cl.[CH3:32]O>CO>[OH:4][C:5]1[C:13]([CH:14]=[O:15])=[CH:12][C:11]([I:19])=[C:10]2[C:6]=1[CH:7]([O:30][CH3:32])[N:8]([C:21]([CH3:22])([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[CH3:29])[C:9]2=[O:20]

Participants

4

Reactant 2

HCID 21893726Hydrochloride methanolHCID 68489206HCID 68489206, compound

Product 1

HCID 86628295HCID 86628295, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Methoxymethoxy-5-dimethoxymethyl-3-hydroxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone (490 mg, 0.929 mmol) was dissolved in methanol (10 mL), and the solution was treated with 10% hydrogen chloride-methanol solution (5 mL), followed by stirring at room temperature for 3 hours. The solvent was evaporated under reduced pressure and the residue was dissolved in acetonitrile (5 mL). The solution was added with 1 mol/L hydrochloric acid (5 mL) and stirred at room temperature for 1 hour. The precipitated solid was collected by filtration and washed with water, followed by drying under reduced pressure to obtain 4-hydroxy-5-formyl-3-methoxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone (329 mg, yield 79%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in acetonitrile (5 mL)
  3. additionThe solution was added with 1 mol/L hydrochloric acid (5 mL)
  4. stirringstirred at room temperature for 1 hour
  5. filtrationThe precipitated solid was collected by filtration
  6. washwashed with water
  7. customby drying under reduced pressure

Sources & evidence

ORD record
ord-8d965707b7cb44bcb339cf9e8020bc5b
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

Loading…