alpha-(1-hydroxy-2-methyl-3-oxoisoindolin-1-yl)-N-methyl-o-toluamide → Mls003116016

HRID 2419646Notes

Reaction equation

HRID 2419646 reaction equation
O[C:2]1([CH2:13][C:14]2[C:15]([C:20]([NH:22][CH3:23])=[O:21])=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH3:12]>S(=O)(=O)(O)O>[CH3:12][N:3]1[C:2]2([CH2:13][C:14]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:20](=[O:21])[N:22]2[CH3:23])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]1=[O:11]

Participants

3

Reactant 1

HCID 20314321alpha-(1-hydroxy-2-methyl-3-oxoisoindolin-1-yl)-N-methyl-o-toluamide

Product 1

HCID 334513Mls003116016

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A mixture of 9.1 grams (0.0294 mole) of α-(1-hydroxy-2-methyl-3-oxoisoindolin-1-yl)-N-methyl-o-toluamide and 180 milliliters of 2 M sulfuric acid is refluxed for 20 hours. The mixture is cooled and the solid separated by filtration. The solid is then dissolved in methylene chloride and washed twice with water and once with brine. The organic phase is dried over magnesium sulfate, filtered and evaporated in vacuo. The resulting oil is crystallized from ethanol to give 2,2'-dimethyl spiro[isoindolin-1,3'(4'H)-isoquinoline]1',3-dione, m.p. 202° - 203° C.

Workup

  1. temperatureis refluxed for 20 hours
  2. temperatureThe mixture is cooled
  3. customthe solid separated by filtration
  4. dissolutionThe solid is then dissolved in methylene chloride
  5. washwashed twice with water and once with brine
  6. dry with materialThe organic phase is dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe resulting oil is crystallized from ethanol

Sources & evidence

ORD record
ord-828fa163c24448f1ba1854bebcb5c5a6
Source dataset
uspto-grants-1978_08
Patent number
US04107311

Reaction notes

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