Methyl iodide → Ethyl 5-chloro-2-methyl-3-phenyl-2H-isoindole-1-carboxylate

HRID 1112499Notes

Reaction equation

HRID 1112499 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:9]2[C:14]=1[CH:13]=[CH:12][C:11]([Cl:15])=[CH:10]2)=[O:5])[CH3:2].[C:22](=O)([O-])[O-].[K+].[K+].CI>CS(C)=O>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:22])[C:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:9]2[C:14]=1[CH:13]=[CH:12][C:11]([Cl:15])=[CH:10]2)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 54174784Ethyl 5-chloro-3-phenyl-2H-isoindole-1-carboxylate

Product 1

HCID 54012509Ethyl 5-chloro-2-methyl-3-phenyl-2H-isoindole-1-carboxylate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A suspension of 15 g. of 5-chloro-3-phenylisoindole-1-carboxylic acid ethyl ester in 150 ml. of dimethylsulfoxide is treated under an atmosphere of argon at 15°-20° C. with 13.8 g. of finely ground dry potassium carbonate and 14 ml. of methyl iodide, the mixture is stirred intensively at room temperature for 1 hour and then poured on to 750 ml. of ice-water. After the addition of 35 g. of sodium chloride, the precipitated product is removed by filtration, washed with water and dissolved in methylene chloride. The organic phase is dried over sodium sulfate and evaporated. The residue crystallizes upon trituration with hexane. Recrystallization from ethanol yields 5-chloro-2-methyl-3-phenylisoindole-1-carboxylic acid ethyl ester in the form of almost colorless crystals having a melting point of 94°-96° C.

Workup

  1. additionA suspension of 15 g
  2. additionpoured on to 750 ml
  3. additionAfter the addition of 35 g
  4. customof sodium chloride, the precipitated product is removed by filtration
  5. washwashed with water
  6. dissolutiondissolved in methylene chloride
  7. dry with materialThe organic phase is dried over sodium sulfate
  8. customevaporated
  9. customThe residue crystallizes upon trituration with hexane
  10. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-133b9164249e4aafaf6a328e2955898e
Source dataset
uspto-grants-1978_10
Patent number
US04122265

Reaction notes

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