3-(乙氨基)苯酚

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A 1.0 M solution of borane-methyl sulfide in dichloromehtane (275 ml) was added dropwise to a solution of 3-acetamidophenol (161 g) in THF (800 ml) over about 1 to 2 hours. The mixture was heated to reflux temperature for about 4 hours and was then poured slowly into methanol (1 liter). The solvent was evaporated to a heavy syrup, which deposited crystals on cooling and scratching. The solid was collected by filtration and redissolved in methanol. Evaporation and recrystallization as above gave a 74% yield of the compound. The mixture was heated to reflux temperature for about 4 hours The solvent was evaporated to a heavy syrup, which on cooling The solid was collected by filtration redissolved in methanol Evaporation and recrystallization as

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: This compound was obtained (yield 47%) based on the method described in Production Example 1B using 6-butoxy-2,4-dichloro-1,3,5-triazine instead of the 2,4-dichloro-6-ethyl-1,3,5-triazine, and using 3-ethylaminophenol instead of the 3-aminophenol. This compound was obtained (yield 47%)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: This compound was obtained (yield 43%) based on the method described in Production Example 2B using 4,6-dichloro-2-methylthio-pyrimidine instead of the 4,6-dichloro-2-ethylpyrimidine, and using 3-ethylaminophenol instead of the 3-aminophenol. This compound was obtained (yield 43%)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: This compound was obtained (yield 43%) based on the method described in Production Example 2B using 4,6-dichloro-2-methylthio-pyrimidine instead of the 4,6-dichloro-2-ethylpyrimidine, and using 3-ethylaminophenol instead of the 3-aminophenol. This compound was obtained (yield 43%)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A 1.0 M solution of borane-methyl sulfide in dichloromehtane (275 ml) was added dropwise to a solution of 3-acetamidophenol (161 g) in THF (800 ml) over about 1 to 2 hours. The mixture was heated to reflux temperature for about 4 hours and was then poured slowly into methanol (1 liter). The solvent was evaporated to a heavy syrup, which deposited crystals on cooling and scratching. The solid was collected by filtration and redissolved in methanol. Evaporation and recrystallization as above gave a 74% yield of the compound. The mixture was heated to reflux temperature for about 4 hours The solvent was evaporated to a heavy syrup, which on cooling The solid was collected by filtration redissolved in methanol Evaporation and recrystallization as

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A 1.0 M solution of borane-methyl sulfide in dichloromehtane (275 ml) was added dropwise to a solution of 3-acetamidophenol (161 g) in THF (800 ml) over about 1 to 2 hours. The mixture was heated to reflux temperature for about 4 hours and was then poured slowly into methanol (1 liter). The solvent was evaporated to a heavy syrup, which deposited crystals on cooling and scratching. The solid was collected by filtration and redissolved in methanol. Evaporation and recrystallization as above gave a 74% yield of the compound. The mixture was heated to reflux temperature for about 4 hours The solvent was evaporated to a heavy syrup, which on cooling The solid was collected by filtration redissolved in methanol Evaporation and recrystallization as

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: This compound was obtained (yield 47%) based on the method described in Production Example 1B using 6-butoxy-2,4-dichloro-1,3,5-triazine instead of the 2,4-dichloro-6-ethyl-1,3,5-triazine, and using 3-ethylaminophenol instead of the 3-aminophenol. This compound was obtained (yield 47%)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: This compound was obtained (yield 43%) based on the method described in Production Example 2B using 4,6-dichloro-2-methylthio-pyrimidine instead of the 4,6-dichloro-2-ethylpyrimidine, and using 3-ethylaminophenol instead of the 3-aminophenol. This compound was obtained (yield 43%)

反应条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Methyl bromoacetate (10.7 g, 70 mmole), 3-(ethylamino) phenol from above (4.8 g, 35 mmole), and ethyl diisopropyl amine (4.45 g, 35 mmole) were combined in 25 ml of toluene. The mixture was heated at 100° C. for 30 min. and then evaporated under vacuum and chromatographed on a silica gel column using 5% (v/v) methanol/methylene chloride. The combined fractions were washed with saturated sodium bicarbonate and neutralized with 0.1N HCL. The combined fractions were dried over Na2SO4 and evaporated to give 7.24 g of N-ethyl-N-3-hydroxyphenyl glycine methyl ester. evaporated under vacuum chromatographed on a silica gel column The combined fractions were washed with saturated sodium bicarbonate and neutralized with 0.1N HCL The combined fractions were dried over Na2SO4 evaporated

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of 161 g of 3-acetamidophenol in 800 ml of tetrahydrofuran was added dropwise over 1-2 hr 275 ml of a 1.0M solution of borane-methyl sulfide in dichloromethane. The reaction was heated to reflux 4-5 hr and then poured slowly into 1 l of methanol. The solvent was evaporated to a heavy syrup which deposited crystals on cooling and scratching. The solid was collected by filtration and redisolved in methanol. Evaporation and crystallization as above gave a 74% yield of 3-(ethylamino) phenol. The reaction was heated to reflux 4-5 hr The solvent was evaporated to a heavy syrup which on cooling The solid was collected by filtration Evaporation and crystallization as

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: This compound was obtained (yield 47%) based on the method described in Production Example 1B using 6-butoxy-2,4-dichloro-1,3,5-triazine instead of the 2,4-dichloro-6-ethyl-1,3,5-triazine, and using 3-ethylaminophenol instead of the 3-aminophenol. This compound was obtained (yield 47%)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: This compound was obtained (yield 43%) based on the method described in Production Example 2B using 4,6-dichloro-2-methylthio-pyrimidine instead of the 4,6-dichloro-2-ethylpyrimidine, and using 3-ethylaminophenol instead of the 3-aminophenol. This compound was obtained (yield 43%)