6-AMino-2,3-dihydroisoindol-1-one Chemical Properties

Melting point:

247 °C

Boiling point:

499.9±45.0 °C(Predicted)

Density 

1.307±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

14.77±0.20(Predicted)

Appearance

Light yellow to green yellow Solid

Safety Information

HS Code 

2933998090

6-AMino-2,3-dihydroisoindol-1-one Usage And Synthesis

Uses

6-AMino-2,3-dihydroisoindol-1-one is used in the synthesis of a novel potent glycoprotein IIb-IIIa (GP IIb-IIIa) receptor antagonist based on the isoindolone skeleton.

Synthesis

General procedure for the synthesis of 6-amino-isoindolin-1-one from 6-nitro-isoindolin-1-one: A suspension of intermediate 6B (1.6 g, 8.98 mmol) and Pd/C (0.18 g) in methanol (100 mL) was stirred for 4 hr under hydrogen (1 atm) atmosphere. After completion of the reaction, the reaction mixture was filtered and the filter cake was washed with methanol. After combining the filtrates, the solvent was removed by concentration under reduced pressure. The crude product was ground with methanol (10 mL) and subsequently dried under reduced pressure to afford intermediate 6 (800 mg, 5.40 mmol, 60.1% yield) as a beige solid. The structure of the product was confirmed by 1H NMR (400 MHz, DMSO-d6): δ 4.15 (s, 2H), 5.26 (s, 2H), 6.77 (dd, J = 8.25, 2.20 Hz, 1H), 6.80 (s, 1H), 7.16 (d, J = 8.79 Hz, 1H), 8.29 (s, 1H). The mass spectrum (ESI) showed m/z 149.2 ([M + H]+).

References

[1] Patent: WO2008/79759, 2008, A1. Location in patent: Page/Page column 91-92
[2] Patent: WO2008/79836, 2008, A2. Location in patent: Page/Page column 87
[3] Chemische Berichte, 1934, vol. 67, p. 675,681
[4] Patent: WO2010/10184, 2010, A1. Location in patent: Page/Page column 59
[5] Patent: US2004/58970, 2004, A1. Location in patent: Page 14

6-AMino-2,3-dihydroisoindol-1-one(675109-45-2)Related Product Information

• 4-nitroisoindolin-1-one
• 4-Nitrophthalimide
• 4-Nitro-N-methylphthalimide
• 4-Aminophthalimide
• 4-Chloro-5-nitrophthalimide
• N-CHLOROMETHYL-4-NITROPHTHALIMIDE
• 4,5-DIANILINOPHTHALIMIDE
• 4-AMINO-N-METHYLPHTHALIMIDE
• 4-(5-AMINO-1,3-DIOXO-1,3-DIHYDRO-ISOINDOL-2-YL)-BENZOIC ACID METHYL ESTER
• 5-AMINO-2-P-TOLYL-ISOINDOLE-1,3-DIONE
• (5-NITRO-1,3-DIOXO-1,3-DIHYDRO-2H-ISOINDOL-2-YL)ACETIC ACID
• 4-NITRO-N-PHENYLPHTHALIMIDE
• N-(O-NITROPHENYL)4-NITROPHTHALIMIDE
• 5-AMINO-2-NAPHTHALEN-2-YL-ISOINDOLE-1,3-DIONE
• 4-(5-NITRO-1,3-DIOXO-1,3-DIHYDRO-2H-ISOINDOL-2-YL)BUTANOIC ACID
• 5-(ethylamino)-2-methyl-2,3-dihydro-1H-isoindole-1,3-dione
• 5-AMINO-2-NAPHTHALEN-1-YL-ISOINDOLE-1,3-DIONE
• 5-amino-2-phenyl-2,3-dihydro-1H-isoindole-1,3-dione