1104
Rádl, Hezký, Konvička, Krejčí:
[(3-Am in o-2-ben zoyl-1-ben zofuran -7-yl)oxy]acetic Acid (7b)
An aqueous solution (30 m l) of sodium h ydroxide (1.6 g, 40 m m ol) was added to a stirred
suspen sion of 7a (1.7 g, 5 m m ol) in m eth an ol (50 m l) an d th e m ixture was stirred at room
tem perature for 24 h . Th e solution was acidified with dilute h ydroch loric acid, th e m ixture
was cooled an d th e in soluble portion was filtered off. Crystallization from eth an ol provided
7b (0.75 g, 48%) as yellowish crystals; m .p. 191–195 °C. For C17H13NO5 (311.3) calculated:
65.59% C, 4.21% H, 4.50% N; foun d: 65.33% C, 4.48% H, 4.77% N. 1H NMR (DMSO-d6):
4.90 s, 2 H (CH2); 7.08 bd, 1 H, J = 8.0, 0.9 (H-6); 7.19 t, 1 H, J = 7.8 (H-4′); 7.30 bs, 2 H
(NH2); 7.59 m , 4 H (H-4, H-5, H-3′, H-5′); 8.12 dd, 2 H, J = 7.8, 2.2 (H-2′, H-6′).
{4-[(3-Am in o-1-ben zofuran -2-yl)carbon yl]ph en oxy}acetic Acid (7e)
Accordin g to th e procedure described for th e preparation of 7b, com poun d 7d was h ydro-
lyzed to give 7e (54%) as yellowish crystals; m .p. 215–218 °C (eth an ol). For C17H13NO5
(311.3) calculated: 65.59% C, 4.21% H, 4.50% N; foun d: 65.39% C, 4.36% H, 4.37% N.
1H NMR (DMSO-d6): 4.40 s, 2 H (CH2); 7.10 dt, 2 H, J = 9.1, 2.7 (H-3′, H-5′); 7.26 bs, 2 H
(NH2); 7.31 m , 1 H (H-6); 7.53–7.59 m , 2 H (H-5, H-7); 8.04 d, 1 H, J = 7.9 (H-4); 8.18 dt,
2 H, J = 9.1, 2.7 (H-2′, H-6′).
2-Ben zoyl-7-[3-(dim eth ylam in o)propoxy]-1-ben zofuran -3-am in e (7c)
A stirred m ixture of 4d (2.5 g, 10 m m ol), potassium carbon ate (2.8 g, 20 m m ol), 3-(di-
m eth ylam in o)propyl ch loride h ydroch loride (2.0 g, 12.7 m m ol), an d 2-butan on e (80 m l)
was refluxed for 30 h (TLC m on itorin g). Th e in soluble portion was filtered off, th e solid was
wash ed with h ot butan on e an d th e filtrate was evaporated. Th e residue was purified by flash
ch rom atograph y (silica gel, petroleum eth er–aceton e from 7 : 3 to 1 : 1) followed by crystal-
lization from h exan e to give 7c as yellowish crystals (1.8 g, 53%); m .p. 87–91 °C. For
C
20H22N2O3 (338.4) calculated: 70.99% C, 6.55% H, 8.28% N; foun d: 71.25% C, 6.88% H,
8.30% N. 1H NMR (CDCl3): 2.08 m , 2 H (CH2); 2.31 s, 6 H (CH3); 2.58 t, 2 H, J = 7.3
(CH2N); 4.27 t, 2 H, J = 6.3 (CH2O); 5.96 bs, 2 H (NH2); 7.01 dd, 1 H, J = 7.0, 1.9 (H-6);
7.16 t, 1 H, J = 7.8, 7.0 (H-5); 7.20 dd, 1 H, J = 7.8, 1.9 (H-4); 7.52 m , 3 H (H-3′, H-4′, H-5′);
8.29 m , 2 H (H-2′, H-6′).
A part of th e base was con verted to h ydrogen m aleate; m .p. 197–199 °C. For C24H26N2O7
(454.5) calculated: 63.43% C, 5.77% H, 6.16% N; foun d: 63.76% C, 6.01% H, 6.39% N.
2-{4-[3-(Dim eth ylam in o)propoxy]ben zoyl}-1-ben zofuran -3-am in e (7f)
Accordin g to th e procedure described for th e preparation of 7c, usin g th e sam e am oun t of
4e, com poun d 7f was prepared as yellow crystallin e m on oh ydrate (2.1 g, 59%); m .p. 73–
78 °C (h exan e). For C20H24N2O4 (356.4) calculated: 67.40% C, 6.79% H, 7.86% N; foun d:
67.19% C, 7.17% H, 7.65% N. 1H NMR (CDCl3): 2.03 q, 2 H (CH2); 2.31 s, 6 H (CH3); 2.53 t,
2 H, J = 7.3 (CH2N); 4.13 t, 2 H, J = 6.3 (CH2O); 5.95 bs, 2 H (NH2); 7.01 d, 2 H, J = 9.0
(H-3′, H-5′); 7.27 ddd, 1 H, J = 8.1, 6.6, 1.6 (H-6); 7.49 m , 2 H (H-5, H-7); 7.62 d, 1 H, J = 7.8
(H-4); 8.29 d, 2 H, J = 9.0 (H-2′, H-6′).
A part of th e base was con verted to h ydrogen m aleate; m .p. 137–139 °C. For C24H26N2O7
(454.5) calculated: 63.43% C, 5.77% H, 6.16% N; foun d: 63.73% C, 5.91% H, 6.16% N.
Collect. Czech. Chem. Commun. (Vol. 65) (2000)