Ethyl Acetate → Methyl beta-phthalimido-beta-(4-methylphenyl)propionate

HRID 745249Notes

Reaction equation

HRID 745249 reaction equation
Cl.[NH2:2][CH:3]([C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)[CH2:4][C:5]([O:7][CH3:8])=[O:6].C([O:19][CH2:20][CH3:21])(=O)C>C(N(CC)CC)C>[C:20]1(=[O:19])[N:2]([CH:3]([C:9]2[CH:10]=[CH:11][C:12]([CH3:15])=[CH:13][CH:14]=2)[CH2:4][C:5]([O:7][CH3:8])=[O:6])[C:5](=[O:6])[C:4]2=[CH:3][CH:9]=[CH:10][CH:11]=[C:21]12

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 17517621HCID 17517621, compound

Product 1

HCID 13655327Methyl beta-phthalimido-beta-(4-methylphenyl)propionate

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To 14 g of methyl β-amino-β-(4-methylphenyl)propionate hydrochloride, were added 200 ml of ethyl acetate and 10.2 ml of triethylamine. The mixture was stirred at room temperature for 30 minutes, then washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and filtered. The filtrate was evaporated under reduced pressure. To the residue, was added 8.5 g of phthalic anhydride. The mixture was stirred at 150° to 155° C. for one hour and recrystallized from an ether-n-hexane mixture to yield 15 g of methyl β-phthalimido-β-(4-methylphenyl)propionate; m.p. 97°-99° C.

Workup

  1. washwashed with saturated aqueous sodium chloride solution
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customThe filtrate was evaporated under reduced pressure
  5. additionTo the residue, was added 8.5 g of phthalic anhydride
  6. stirringThe mixture was stirred at 150° to 155° C. for one hour
  7. customrecrystallized from an ether-n-hexane mixture

Sources & evidence

ORD record
ord-66a64d02b43a46558b84213d36509703
Source dataset
uspto-grants-1986_07
Patent number
US04598077

Reaction notes

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