Electric Literature of 7147-90-2,Some common heterocyclic compound, 7147-90-2, name is 5-Chloroisoindoline-1,3-dione, molecular formula is C8H4ClNO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
4-Chlorophthalimide (273 mg) is dissolved in a minimum of boiling ethanol (ca. 2.5 ml). 37% formaldehyde solution (0.15 ml) is added to the still hot solution followed by N-(4-chlorophenyl)glycine (279 mg). Reflux is continued for 3 h. The yellow solution is kept in the refrigerator overnight. The yellow precipitate is collected by suction filtration, washed with ethanol, and dried in vacuo. The crude is recrystallised from ethanol to provide N-[(5-chloro-1,3-dioxo-2-isondolinyl)methyl]-N-(4-chlorophenyl)glycine (135 mg) as light yellow crystals. 1H-NMR (500 MHz, DMSO-d6): delta (ppm)=4.26 (s, 2H), 5.24 (s, 2H), 6.97 (d, J=9.1 Hz, 2H), 7.22 (d, J=9.1 Hz, 2H), 7.90 (d, J=1.2 Hz, 2H), 7.97 (t, J=1.2 Hz, 1H), 12.71 (br s, 1H).13C-NMR and DEPT (125 MHz, DMSO-d6): delta (ppm)=51.77 (CH2), 54.72 (CH2), 114.39 (2CH), 121.70 (C), 123.35 (CH), 124.99 (CH), 128.39 (2CH), 129.97 (C), 133.41 (C), 134.38 (CH), 139.41 (C), 145.34 (C), 167.01 (CO), 167.35 (CO), 171.48 (CO).MS (+ESI): m/z=379 (M+H).
The synthetic route of 7147-90-2 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; UNIVERSITAET DES SAARLANDES; US2012/46307; (2012); A1;,
Indoline – Wikipedia,
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