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

HRID 1641348Notes

Reaction equation

HRID 1641348 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-d767c52409534ba89000dbb4f4d3c448
Source dataset
uspto-grants-2012_02
Patent number
US08114878B2

Reaction notes

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