Trimellitic anhydride → 2-(2-Morpholinoethyl)-1,3-dioxoisoindoline-5-carboxylic acid

HRID 252876

Reaction equation

HRID 252876 reaction equation
[CH:1]1[C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]2[C:10]([O:12][C:13](=[O:14])[C:3]=2[CH:2]=1)=O.[NH2:15][CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1>C(O)(=O)C>[O:21]1[CH2:22][CH2:23][N:18]([CH2:17][CH2:16][N:15]2[C:10](=[O:12])[C:4]3[C:3](=[CH:2][CH:1]=[C:6]([C:7]([OH:9])=[O:8])[CH:5]=3)[C:13]2=[O:14])[CH2:19][CH2:20]1

Participants

4

Reactant 2

HCID 11089Trimellitic anhydrideHCID 4082852-Morpholinoethylamine

Product 1

HCID 597368682-(2-Morpholinoethyl)-1,3-dioxoisoindoline-5-carboxylic acidYield 82%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1,2,4-Benzenetricarboxylic anhydride (356, 0.487 g, 2.53 mmol) and 4-(2-aminoethyl)morpholine (0.33 g, 2.53 mmol) were allowed to stir 2 hours at 130° C. in acetic acid (10 mL). The reaction mixture was then cooled to room temperature and the precipitated solid was collected by filtration, washed with H2O and dried under vacuum, to afford title compound 357 as a white powder (0.63 g, 82% yield). 1H NMR (DMSO) δ (ppm): 8.26 (dd, J=7.6, 1.4 Hz, 1H), 8.15 (dd, J=1.4, 0.6 Hz, 1H), 7.92 (dd, J=7.6, 0.6 Hz, 1H), 3.73 (t, J=6.5 Hz, 2H), 3.50 (t, J=4.5 Hz, 4H), 2.59 (t, J=6.5 Hz, 2H), 2.47 (overlapped with DMSO, 4H). MS: 304.3 (calc), 305.1 (obs).

Workup

  1. filtrationthe precipitated solid was collected by filtration
  2. washwashed with H2O
  3. customdried under vacuum

Sources & evidence

ORD record
ord-45c99c82dd824e318b094a53657e5daa
Source dataset
uspto-grants-2011_01
Patent number
US07868205B2

Linked notes

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