Methanol → 3-Hydroxy-2-phenethyl-5,6-dimethoxy-2,3-dihydro-1H-isoindol-1-one

HRID 65691

Reaction equation

HRID 65691 reaction equation
[BH4-].[K+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[O:13])[N:11]([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:9](=[O:10])[C:8]2=[CH:22][C:23]=1[O:24][CH3:25].O1CCOCC1.CO>O>[OH:13][CH:12]1[C:7]2[C:8](=[CH:22][C:23]([O:24][CH3:25])=[C:5]([O:4][CH3:3])[CH:6]=2)[C:9](=[O:10])[N:11]1[CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 312751,4-DioxaneHCID 4192641Potassium borohydrideHCID 227575535,6-Dimethoxy-2-(2-phenylethyl)-1H-isoindole-1,3(2H)-dione

Product 1

HCID 227575543-Hydroxy-2-phenethyl-5,6-dimethoxy-2,3-dihydro-1H-isoindol-1-oneYield 96.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Potassium borohydride (4.87 g) dissolved in distilled water (58.7 cc) is added to 4,5-dimethoxy-N-phenethyl phthalimide (28 g) suspended in a mixture (180 cc) consisting of equal volumes of dioxan and methanol. The reaction mixture is heated under reflux for 2 hours and then concentrated to a volume of 60 cc and distilled water (450 cc) is added. After cooling, the resulting precipitate is filtered off, washed three times with distilled water (total 1000 cc) and dried under reduced pressure (20 mm Hg) at 25° C. 3-Hydroxy-2-phenethyl-5,6-dimethoxy-2,3-dihydro-1H-isoindol-1-one (27.3 g), melting at 130° C., is thus obtained.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureunder reflux for 2 hours
  3. concentrationconcentrated to a volume of 60 cc
  4. distillationdistilled water (450 cc)
  5. additionis added
  6. temperatureAfter cooling
  7. filtrationthe resulting precipitate is filtered off
  8. washwashed three times with distilled water (total 1000 cc)
  9. customdried under reduced pressure (20 mm Hg) at 25° C

Sources & evidence

ORD record
ord-8df3739a1b454da3873c39b824b653b5
Source dataset
uspto-grants-1978_12
Patent number
US04128650

Linked notes

Loading…