2-(3-(2-Phenyl-1,3-dioxolan-2-yl)propyl)isoindoline-1,3-dione → HCID 23123945, compound

HRID 1013121Notes

Reaction equation

HRID 1013121 reaction equation
[C:1]1([C:7]2([CH2:12][CH2:13][CH2:14][N:15]3C(=O)C4C(=CC=CC=4)C3=O)[O:11][CH2:10][CH2:9][O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CN.CO>[C:1]1([C:7]2([CH2:12][CH2:13][CH2:14][NH2:15])[O:11][CH2:10][CH2:9][O:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 574477532-(3-(2-Phenyl-1,3-dioxolan-2-yl)propyl)isoindoline-1,3-dione

Product 1

HCID 23123945HCID 23123945, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6329MethylamineSolvent

Conditions

Temperature
50 °C

Procedure

Dissolve 2-[3-(2-phenyl-[1,3]dioxolan-2-yl)-propyl]-isoindole-1,3-dione (38 g, 112.91 mmol) in 2 M methylamine solution in methanol (300 mL) and heat in a sealed tube for 3 h at 50° C. Cool the solution to RT, concentrate and purify (silica gel chromatography, eluting with 25:75 DCM:2 M ammonia in methanol) to give the title compound as an oil (11 g, 47%).

Workup

  1. temperatureCool the solution to RT
  2. concentrationconcentrate
  3. custompurify
  4. wash(silica gel chromatography, eluting with 25:75 DCM:2 M ammonia in methanol)

Sources & evidence

ORD record
ord-fee58fb23f764427b57a61836060b4de
Source dataset
uspto-grants-2011_07
Patent number
US07981882B2

Reaction notes

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