ChemicalBook CAS DataBase List 4-AMINO-N-BUTYL PHTHALIMIDINE

4-AMINO-N-BUTYL PHTHALIMIDINE synthesis

7synthesis methods

Product Name:4-AMINO-N-BUTYL PHTHALIMIDINE
CAS Number:68930-97-2
Molecular formula:C12H14N2O2
Molecular Weight:218.25

54395-37-8 Synthesis

54395-37-8
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68930-97-2
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Yield:68930-97-2 750 mg (59%)

Reaction Conditions:

with sodium carbonate in methanol;water;

Steps:

4-[3-(2-Butyl-1,3-dioxo-2,3-dihydro-1H-isoindol-5-yl)-1-(4-tert-butylphenyl)ureidomethyl]-N-(2H-tetrazol-5-yl)benzamide

A solution of N-butyl-4-nitrophthalimide (1.45 g, 5.8 mmol) in methanol (30 mL) was added drop wise to a well stirred solution of sodium dithionite (6.50 g, 37.1 mmol) and sodium carbonate (3.22 g, 30.5 mmol) in water (40 mL), while the temperature was maintained at 70° C. After addition, heating at 70° C. was continued for a further 30 minutes, then the reaction mixture was allowed to cool to room temperature. The reaction volume was reduced to one third by rotary evaporation, and the residual water solution was extracted with diethyl ether (2*50 mL). The combined organic phases were dried with anhydrous Na₂SO₄, and then taken to dryness. The residual oil was recrystallized from ethanol/water to give 750 mg (59%) of N-butyl-4-aminophthalimide. ¹H NMR (DMSO-d₆): δ0.89 (t, 3H); 1.26 (m, 2H); 1.53 (m, 2H); 3.48 (t, 2H); 6.44 (bs, 2H); 6.78 (dd, 1H); 6.92 (d,1H); 7.46 (d, 1H).

References:

US6503949,2003,B1