[2-(2-aminoethyl)phenyl]methanol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-Amino-2-(2-hydroxymethylphenyl)ethane and 4-trifluoromethylbenzoyl chloride were successively reacted in the same way as in steps (b) and (c) of Example 12 to afford 1-(4-trifluoromethylbenzoyl)amino-2-(2-hydroxymethylphenyl)ethane having a melting point of 145.8° to 146.3° C. The product was successively reacted in the same way as in steps (d), (e), (f) and (g) of Example 12 to afford 1-(4-trifluoromethylphenyl)isoquinoline-5-acetonitrile having a melting point of 121.9° to 122.6° C.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-Amino-2-(2-hydroxymethylphenyl)ethane and cyclobutanecarbonyl chloride were successively reacted in the same way as in steps (b) and (c) of Example 12 to afford 1-cyclobutylcarbonylamino-2-(2-hydroxymethylphenyl)ethane as in oil. The product was successively reacted in the same way as in steps (d), (e), (f) and (g) of Example 12 to afford 1-cyclobutylisoquinoline-5-acetonitrile. The product was treated in the same way as in Example 3 to afford 1-cyclobutylisoquinoline-5-acetic acid having a decomposition point of 202.8° to 209.8° C.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-Amino-2-(2-hydroxymethylphenyl)ethane and butyryl chloride were successively reacted in the same way as in steps (b) and (c) of Example 12 to afford 1-butyrylamino-2-(2-hydroxymethylphenyl)ethane as an oil. The product was successively reacted in the same way as in steps (d), (e), (f) and (g) of Example 12 to afford 1-n-propylisoquinoline-5-acetonitrile.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-Amino-2-(2-hydroxymethylphenyl)ethane and isovaleryl chloride were successively reacted in the same way as in steps (b) and (c) of Example 12 to afford 1-isovalerylamino-2-(2-hydroxymethylphenyl)ethane. The product was successively reacted in the same way as in steps (d), (e), (f), and (g) of Example 12 to afford 1-isobutylisoquinoline-5-acetonitrile as an oil.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-Amino-2-(2-hydroxymethylphenyl)ethane (10.2 g) was dissolved in 40 ml of pyridine, and with stirring under ice cooling, 25 g of 4-nitrobenzoyl chloride was added gradually. The mixture was stirred at room temperature for 4 hours and then at 50° C. for 1 hour, and poured into ice water. The crystals precipitated were washed in water, dried, and recrystallized from tetrahydrofuran-benzene to afford 24.3 g of 1-(4-nitrobenzoyl)-amino-2-[2-(4-nitrobenzoyloxymethyl)phenyl]ethane having a melting point of 168.2° to 169.7° C. The mixture was stirred at room temperature for 4 hours The crystals precipitated were washed in water dried recrystallized from tetrahydrofuran-benzene

Conditions: temp:-20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: One hundred and fifty (150) grams of methyl 2-cyanomethylbenzoate ("Yakugaku Zasshi", Vol. 86, p. 544, 1966) was added dropwise to a suspension of 60 g of lithium aluminum hydride and 211 g of aluminium chloride in ether while maintaining the suspension at -20° C. The mixture was stirred at room temperature for 5 hours, and the aluminum complex was decomposed with 520 ml of a 10 N aqueous solution of sodium hydroxide and 140 ml of water. The residue was extracted with tetrahydrofuran, dried, and distilled under reduced pressure to afford 45 g of 1-amino-2-(2-hydroxymethylphenyl)ethane as a colorless oil having a boiling point of 125° C./0.5 mmHg. The residue was extracted with tetrahydrofuran dried distilled under reduced pressure