Triethylamine → Ethyl 3-[5-methyl-1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl]propionate

HRID 1814625Notes

Reaction equation

HRID 1814625 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[O:10])[O:8][C:6](=O)[C:5]2=[CH:11][CH:12]=1.Cl.[NH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].C(N(CC)CC)C>CN1C(=O)CCC1.O>[CH3:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:11][CH:12]=1)[C:6](=[O:8])[N:14]([CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:9]2=[O:10]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 880694-Methylphthalic anhydrideHCID 458475beta-Alanine, ethyl ester, hydrochloride

Product 1

HCID 22501918Ethyl 3-[5-methyl-1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl]propionateYield 80.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
130 °C

Procedure

A solution of 4-methylphthalic anhydride (21.3 g, 0.13 mol), ethyl 3-aminopropionate hydrochloride (20.2 g, 0.13 mol), and triethylamine (19 mL) in NMP was stirred at ambient temperature for 3 days, and heated to 130° C. for 3 hours. The mixture was diluted with water (300 mL), and extracted with ethyl acetate (3×100 mL). The combined organic extracts were washed with 1N hydrochloric acid (2×50 mL), sodium bicarbonate solution (2×50 mL), dried (MgSO4), and concentrated to give 27.3 g yellow oil.

Workup

  1. extractionextracted with ethyl acetate (3×100 mL)
  2. washThe combined organic extracts were washed with 1N hydrochloric acid (2×50 mL), sodium bicarbonate solution (2×50 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-bb49c2dd484c4d98a959ed2d29f91c2a
Source dataset
uspto-grants-2005_04
Patent number
US06875760B2

Reaction notes

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