ChemicalBook CAS DataBase List 4-AMINOISOINDOLIN-1-ONE

4-AMINOISOINDOLIN-1-ONE synthesis

7synthesis methods

Product Name:4-AMINOISOINDOLIN-1-ONE
CAS Number:366452-98-4
Molecular formula:C8H8N2O
Molecular Weight:148.16

366452-97-3

366452-98-4

General procedure for the synthesis of 4-aminoisoindolin-1-one from 4-nitro-isoindolin-1-one: A mixture of 4-nitro-2,3-dihydro-1H-isoindolin-1-one (20 g), ammonium formate (35 g), and 7.5% Pd/C (0.6 g) in methanol (60 ml) was stirred for 2 hr at 35° C. The reaction was completed by filtration to remove the catalyst. After completion of the reaction, the Pd/C catalyst was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was recrystallized by water to give 15.3 g of light yellow solid product in 92% yield. Melting point: 195.6-197°C. 1H-NMR (300 MHz, DMSO-d6) δ: 4.31 (s, 2H), 6.76 (d, 1H), 7.14 (t, 1H), 6.86 (d, 1H), 5.30 (s, 2H), 8.26 (s, 1H). 1H-NMR (300 MHz, DMSO-d6/D2O 1H-NMR (300MHz, DMSO-d6/D2O) δ: 4.14 (s, 2H), 6.79 (d, 1H), 6.93 (d, 1H), 7.16 (t, 1H) FAB (M + 1): 149 Elemental analysis: theoretical value (%): C 64.85, H 5.44, N 18.91; measured value (%): C 64.96, H 5.61, N 19.02. HPLC test conditions: Chromatography Column: Phenomenex Luna 5u C18 (250 mm×4.6 mm); Flow rate: 1.0 ml/min; Detection wavelength: 230 nm; Mobile phase: Acetonitrile/0.1% Phosphate=15/85 or Acetonitrile/0.01M Ammonium Acetate=10/90; Retention time of the target product: 3.580 min; 4.790 min. Purity of target product: 99.66%.

59382-59-1
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$15.00/5g

366452-98-4
127 suppliers
$43.00/100mg

Yield:-

Steps:

Multi-step reaction with 3 steps
1: 98 percent / N-bromosuccinimide; 2,2'-azobisisobutyronitrile / CH₂Cl₂ / 16 h / Heating
2: 81 percent / ammonia / methanol / 2 h / 20 °C
3: 83 percent / ammonium formate / Pd/C / dimethylformamide / 0.5 h / 100 °C

References:

Jagtap, Prakash G.;Southan, Garry J.;Baloglu, Erkan;Ram, Siya;Mabley, Jon G.;Marton, Anita;Salzman, Andrew;Szabo, Csaba [Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,# 1,p. 81 - 85]

366452-97-3 Synthesis

366452-97-3
111 suppliers
$29.00/100mg

366452-98-4
127 suppliers
$43.00/100mg

References