Water → methyl(Z)-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-methoxy-but-2-enoate

HRID 70104Notes

Reaction equation

HRID 70104 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].Cl[CH2:14][C:15]([O:21][CH3:22])=[CH:16][C:17]([O:19][CH3:20])=[O:18].O>CN(C=O)C>[O:6]=[C:4]1[C:3]2[C:2](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:1](=[O:11])[N:5]1[CH2:14]/[C:15](/[O:21][CH3:22])=[CH:16]/[C:17]([O:19][CH3:20])=[O:18]

Participants

5

Reactant 3

HCID 962WaterHCID 5838182-Butenoic acid, 4-chloro-3-methoxy-, methyl esterHCID 24194345Phthalimide potassium salt

Product 1

HCID 59708416methyl(Z)-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-methoxy-but-2-enoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

18.5 potassium phthalimide are suspended in 50 ml DMF, the mixture is heated to 60° C. and 16.5 g methyl 4-chloro-3-methoxy-but-2-enoate in 50 ml DMF are added. After 2 days the reaction mixture is poured into 500 ml of water. The precipitate formed is suction filtered and washed with water. The residue is dissolved in ethyl acetate, dried and the solution is evaporated to dryness. The residue is triturated with ether. 21.77 g of the product are obtained as a powder.

Workup

  1. customThe precipitate formed
  2. filtrationfiltered
  3. washwashed with water
  4. dissolutionThe residue is dissolved in ethyl acetate
  5. customdried
  6. customthe solution is evaporated to dryness
  7. customThe residue is triturated with ether

Sources & evidence

ORD record
ord-40089829728845ff8fc14aa42052cb59
Source dataset
uspto-grants-2014_09
Patent number
US08822474B2

Reaction notes

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