3-(Benzyloxy)aniline

Beige to tan powder

Following a procedure similar to Example 59, reduction reaction was carried out using ferrous(II) acetate, nickel(II) nitrate or cobalt(III) acetylacetonate as a metal compound. The results are shown in Table 11 below. It was confirmed from the results of Examples 60 to 66 that when an amine such as pyrrolidine was added in catalytic reduction system of the present invention using rhodium/carrier catalyst and using a metal compound such as iron salts, nickel salts or cobalt salts, the reaction rate was dramatically improved, the probability of reduction of functional groups such as benzyl ether which was liable to be reduced was lowered, nitro group was selectively reduced and the yield was increased.Following a procedure similar to Example 59, reduction reaction was carried out using ferrous(II) acetate, nickel(II) nitrate or cobalt(III) acetylacetonate as a metal compound. The results are shown in Table 11 below. It was confirmed from the results of Examples 60 to 66 that when an amine such as pyrrolidine was added in catalytic reduction system of the present invention using rhodium/carrier catalyst and using a metal compound such as iron salts, nickel salts or cobalt salts, the reaction rate was dramatically improved, the probability of reduction of functional groups such as benzyl ether which was liable to be reduced was lowered, nitro group was selectively reduced and the yield was increased.Following a procedure similar to Example 59, reduction reaction was carried out using ferrous(II) acetate, nickel(II) nitrate or cobalt(III) acetylacetonate as a metal compound. The results are shown in Table 11 below. It was confirmed from the results of Examples 60 to 66 that when an amine such as pyrrolidine was added in catalytic reduction system of the present invention using rhodium/carrier catalyst and using a metal compound such as iron salts, nickel salts or cobalt salts, the reaction rate was dramatically improved, the probability of reduction of functional groups such as benzyl ether which was liable to be reduced was lowered, nitro group was selectively reduced and the yield was increased.Following a procedure similar to Example 59, reduction reaction was carried out using ferrous(II) acetate, nickel(II) nitrate or cobalt(III) acetylacetonate as a metal compound. The results are shown in Table 11 below. It was confirmed from the results of Examples 60 to 66 that when an amine such as pyrrolidine was added in catalytic reduction system of the present invention using rhodium/carrier catalyst and using a metal compound such as iron salts, nickel salts or cobalt salts, the reaction rate was dramatically improved, the probability of reduction of functional groups such as benzyl ether which was liable to be reduced was lowered, nitro group was selectively reduced and the yield was increased.Following a procedure similar to Example 59, reduction reaction was carried out using ferrous(II) acetate, nickel(II) nitrate or cobalt(III) acetylacetonate as a metal compound. The results are shown in Table 11 below. It was confirmed from the results of Examples 60 to 66 that when an amine such as pyrrolidine was added in catalytic reduction system of the present invention using rhodium/carrier catalyst and using a metal compound such as iron salts, nickel salts or cobalt salts, the reaction rate was dramatically improved, the probability of reduction of functional groups such as benzyl ether which was liable to be reduced was lowered, nitro group was selectively reduced and the yield was increased.Following a procedure similar to Example 59, reduction reaction was carried out using ferrous(II) acetate, nickel(II) nitrate or cobalt(III) acetylacetonate as a metal compound. The results are shown in Table 11 below. It was confirmed from the results of Examples 60 to 66 that when an amine such as pyrrolidine was added in catalytic reduction system of the present invention using rhodium/carrier catalyst and using a metal compound such as iron salts, nickel salts or cobalt salts, the reaction rate was dramatically improved, the probability of reduction of functional groups such as benzyl ether which was liable to be reduced was lowered, nitro group was selectively reduced and the yield was increased.Following a procedure similar to Example 59, reduction reaction was carried out using ferrous(II) acetate, nickel(II) nitrate or cobalt(III) acetylacetonate as a metal compound. The results are shown in Table 11 below. It was confirmed from the results of Examples 60 to 66 that when an amine such as pyrrolidine was added in catalytic reduction system of the present invention using rhodium/carrier catalyst and using a metal compound such as iron salts, nickel salts or cobalt salts, the reaction rate was dramatically improved, the probability of reduction of functional groups such as benzyl ether which was liable to be reduced was lowered, nitro group was selectively reduced and the yield was increased.3-Benzyloxynitrobenzene (706 mg, 3.08 mmol), pyrrolidine (0.257 mL, 3.08 mmol), 5percent rhodium/carbon powder (190 mg, 0.0924 mmol), nickel(II) nitrate hexahydrate (179 mg, 0.616 mmol) and tetrahydrofuran (20 mL) were placed in a 30 mL eggplant type flask equipped with a magnetic stirrer under nitrogen atmosphere. After the nitrogen gas was substituted with hydrogen gas, the resultant suspension was stirred at room temperature for 2.5 hours under hydrogen atmosphere, and the reaction system was substituted for nitrogen atmosphere. The resultant solid was collected by filtration and washed with tetrahydrofuran. The filtrate and the washing were combined to give a brown solution. The solution was analyzed by high performance liquid chromatography, indicating that 3-benzyloxyaniline was obtained in 92 percent yield (crop 565 mg) and 3-hydroxyaniline in 1 percent yield (crop 3 mg).

Molecular Weight:199.25
XLogP3:3.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:3
Exact Mass:199.099714038
Monoisotopic Mass:199.099714038
Topological Polar Surface Area:35.2
Heavy Atom Count:15
Complexity:177
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes