2-AMINO-N-(3-HYDROXYPROPYL)BENZAMIDE synthesis

Yield:30739-27-6 83%

Reaction Conditions:

in tetrahydrofuran;

Steps:

1 N-(3-Hydroxypropyl)(2-aminophenyl)formamide (1)

EXAMPLE 1 N-(3-Hydroxypropyl)(2-aminophenyl)formamide (1) Isatoic anhydride (6.0 g) and 3-aminopropanol (2.8 ml) were dissolved in tetrahydrofuran (100 ml) and the mixture was stirred at room temperature for 4 hours. Tetrahydrofuran was removed and the residue was purified by silica gel chromatography (ethyl acetate) to obtain 5.94 g of N-(3-hydroxypropyl)(2-aminophenyl)formamide. Yield: 83%. MS (EI, m/z): 194 (M⁺); IR (KBr): 3467, 3358, 3280, 2943, 1627, 1542, 1267, 1062, 930, 748, 686 cm^-1; ¹H NMR (300 MHz, CDCl₃) δ: 1.76(quint,J=6.0), 3.26(1H,brs), 3.58(2H,q,J=6.0), 3.70(2H,q,J=5.5), 5.50(2H,s), 6.52(1H,brs), 6.61-6.69(2H,m), 7.21(1H,dt,J=7.1,1.4), 7.30(1H,dd,J=8.0,1.4).

References:

US6492364,2002,B1