Hydrochloric Acid → 5-(2-Hydroxy-3,4-dimethoxyphenyl)isoindolin-1-one

HRID 2171017Notes

Reaction equation

HRID 2171017 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:21]COC)=[C:5]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[C:16](=[O:20])[NH:15][CH2:14]3)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].Cl>CO>[OH:21][C:4]1[C:3]([O:2][CH3:1])=[C:8]([O:9][CH3:10])[CH:7]=[CH:6][C:5]=1[C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[C:16](=[O:20])[NH:15][CH2:14]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 674677335-(3,4-Dimethoxy-2-(methoxymethoxy)phenyl)isoindolin-1-one

Product 1

HCID 674639885-(2-Hydroxy-3,4-dimethoxyphenyl)isoindolin-1-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a stirring solution of 5-(3,4-dimethoxy-2-(methoxymethoxy)phenyl)isoindolin-1-one (600 g, 1.81 mmol) in methanol (20 mL) at 0° C., was added concentrated hydrochloride acid (1 mL) and the resultant reaction mixture was stirred at 50° C. for 15 min. The reaction mixture was concentrated under reduced pressure and basified with aq sodium bicarbonate solution extracted with ethyl acetate (3×). The combined ethyl acetate layer was washed with brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure. Purification of the resulting residue by washings with ether afforded the title compound as a solid.

Workup

  1. customthe resultant reaction mixture
  2. concentrationThe reaction mixture was concentrated under reduced pressure and basified with aq sodium bicarbonate solution
  3. extractionextracted with ethyl acetate (3×)
  4. washThe combined ethyl acetate layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customPurification of the resulting residue
  8. washby washings with ether

Sources & evidence

ORD record
ord-2f9a5bdac5904cf38b07246842438006
Source dataset
uspto-grants-2015_06
Patent number
US09051290B2

Reaction notes

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