2-(4-chloro-2-methoxyphenyl)ethanamine

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (E)-4-chloro-2-methoxy-1-(2-nitrovinyl)benzene (245 mg, 1.15 mmol) was diluted with THF (1 mL), placed under nitrogen and cooled to 0° C. LAH (4588 μL, 4.59 mmol) was added dropwise and the reaction was stirred for 5 hours warming to ambient temperature. The reaction was cooled to 0° C. and quenched with 174 μL of water, 174 μL of 15% NaOH and 522 μL water. After stirring for 1 hour, ethyl acetate and MgSO4 was added. The reaction mixture was filtered and concentrated to yield 2-(4-chloro-2-methoxyphenyl)ethanamine (160 mg, 0.862 mmol, 75.1% yield). warming to ambient temperature The reaction was cooled to 0° C. quenched with 174 μL of water, 174 μL of 15% NaOH and 522 μL water After stirring for 1 hour ethyl acetate and MgSO4 was added The reaction mixture was filtered concentrated

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

Procedure: A portion of 2-(2-bromo-4-chlorophenyl)acetonitrile (7.1 g; 39.1 mmol) was directly dissolved in borane solution (78.2 mL of a 1.0 M solution in tetrahydrofuran; 78.2 mmol), and the resulting solution was stirred and heated to reflux. After refluxing for a total of 90 minutes, the heat was removed and the solution was allowed to cool for a few minutes, and then 16 mL of methanol was carefully added to quench the solution. The resulting solution was again heated to reflux for 30 minutes. The solvent was then evaporated, and the residue was partitioned between 200 mL of 1M HCl (aq.) and 200 mL ether. The aqueous layer was filtered to remove a small amount of suspended insoluble material, and the pH of the filtrate was adjusted to pH>12 by the addition of 42% NaOH (aq.). The filtrate was then extracted with 200 mL dichloromethane. The organic layer was dried over sodium sulfate and evaporated to give 3.89 g of 2-(4-chloro-2-methoxyphenyl)ethanamine as a colorless liquid. MS (apci, pos) m/z=186. heated to reflux After refluxing for a total of 90 minutes the heat was removed to cool for a few minutes 16 mL of methanol was carefully added to quench the solution The resulting solution was again heated to reflux for 30 minutes The solvent was then evaporated the residue was partitioned between 200 mL of 1M HCl (aq.) and 200 mL ether The aqueous layer was filtered to remove a small amount of suspended insoluble material the pH of the filtrate was adjusted to pH>12 by the addition of 42% NaOH (aq.) The filtrate was then extracted with 200 mL dichloromethane The organic layer was dried over sodium sulfate evaporated

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (E)-4-chloro-2-methoxy-1-(2-nitrovinyl)benzene (245 mg, 1.15 mmol) was diluted with THF (1 mL), placed under nitrogen and cooled to 0° C. LAH (4588 μL, 4.59 mmol) was added dropwise and the reaction was stirred for 5 hours warming to ambient temperature. The reaction was cooled to 0° C. and quenched with 174 μL of water, 174 μL of 15% NaOH and 522 μL water. After stirring for 1 hour, ethyl acetate and MgSO4 was added. The reaction mixture was filtered and concentrated to yield 2-(4-chloro-2-methoxyphenyl)ethanamine (160 mg, 0.862 mmol, 75.1% yield). warming to ambient temperature The reaction was cooled to 0° C. quenched with 174 μL of water, 174 μL of 15% NaOH and 522 μL water After stirring for 1 hour ethyl acetate and MgSO4 was added The reaction mixture was filtered concentrated

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

Procedure: A portion of 2-(2-bromo-4-chlorophenyl)acetonitrile (7.1 g; 39.1 mmol) was directly dissolved in borane solution (78.2 mL of a 1.0 M solution in tetrahydrofuran; 78.2 mmol), and the resulting solution was stirred and heated to reflux. After refluxing for a total of 90 minutes, the heat was removed and the solution was allowed to cool for a few minutes, and then 16 mL of methanol was carefully added to quench the solution. The resulting solution was again heated to reflux for 30 minutes. The solvent was then evaporated, and the residue was partitioned between 200 mL of 1M HCl (aq.) and 200 mL ether. The aqueous layer was filtered to remove a small amount of suspended insoluble material, and the pH of the filtrate was adjusted to pH>12 by the addition of 42% NaOH (aq.). The filtrate was then extracted with 200 mL dichloromethane. The organic layer was dried over sodium sulfate and evaporated to give 3.89 g of 2-(4-chloro-2-methoxyphenyl)ethanamine as a colorless liquid. MS (apci, pos) m/z=186. heated to reflux After refluxing for a total of 90 minutes the heat was removed to cool for a few minutes 16 mL of methanol was carefully added to quench the solution The resulting solution was again heated to reflux for 30 minutes The solvent was then evaporated the residue was partitioned between 200 mL of 1M HCl (aq.) and 200 mL ether The aqueous layer was filtered to remove a small amount of suspended insoluble material the pH of the filtrate was adjusted to pH>12 by the addition of 42% NaOH (aq.) The filtrate was then extracted with 200 mL dichloromethane The organic layer was dried over sodium sulfate evaporated

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (E)-4-chloro-2-methoxy-1-(2-nitrovinyl)benzene (245 mg, 1.15 mmol) was diluted with THF (1 mL), placed under nitrogen and cooled to 0° C. LAH (4588 μL, 4.59 mmol) was added dropwise and the reaction was stirred for 5 hours warming to ambient temperature. The reaction was cooled to 0° C. and quenched with 174 μL of water, 174 μL of 15% NaOH and 522 μL water. After stirring for 1 hour, ethyl acetate and MgSO4 was added. The reaction mixture was filtered and concentrated to yield 2-(4-chloro-2-methoxyphenyl)ethanamine (160 mg, 0.862 mmol, 75.1% yield). warming to ambient temperature The reaction was cooled to 0° C. quenched with 174 μL of water, 174 μL of 15% NaOH and 522 μL water After stirring for 1 hour ethyl acetate and MgSO4 was added The reaction mixture was filtered concentrated

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

Procedure: A portion of 2-(2-bromo-4-chlorophenyl)acetonitrile (7.1 g; 39.1 mmol) was directly dissolved in borane solution (78.2 mL of a 1.0 M solution in tetrahydrofuran; 78.2 mmol), and the resulting solution was stirred and heated to reflux. After refluxing for a total of 90 minutes, the heat was removed and the solution was allowed to cool for a few minutes, and then 16 mL of methanol was carefully added to quench the solution. The resulting solution was again heated to reflux for 30 minutes. The solvent was then evaporated, and the residue was partitioned between 200 mL of 1M HCl (aq.) and 200 mL ether. The aqueous layer was filtered to remove a small amount of suspended insoluble material, and the pH of the filtrate was adjusted to pH>12 by the addition of 42% NaOH (aq.). The filtrate was then extracted with 200 mL dichloromethane. The organic layer was dried over sodium sulfate and evaporated to give 3.89 g of 2-(4-chloro-2-methoxyphenyl)ethanamine as a colorless liquid. MS (apci, pos) m/z=186. heated to reflux After refluxing for a total of 90 minutes the heat was removed to cool for a few minutes 16 mL of methanol was carefully added to quench the solution The resulting solution was again heated to reflux for 30 minutes The solvent was then evaporated the residue was partitioned between 200 mL of 1M HCl (aq.) and 200 mL ether The aqueous layer was filtered to remove a small amount of suspended insoluble material the pH of the filtrate was adjusted to pH>12 by the addition of 42% NaOH (aq.) The filtrate was then extracted with 200 mL dichloromethane The organic layer was dried over sodium sulfate evaporated

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (E)-4-chloro-2-methoxy-1-(2-nitrovinyl)benzene (245 mg, 1.15 mmol) was diluted with THF (1 mL), placed under nitrogen and cooled to 0° C. LAH (4588 μL, 4.59 mmol) was added dropwise and the reaction was stirred for 5 hours warming to ambient temperature. The reaction was cooled to 0° C. and quenched with 174 μL of water, 174 μL of 15% NaOH and 522 μL water. After stirring for 1 hour, ethyl acetate and MgSO4 was added. The reaction mixture was filtered and concentrated to yield 2-(4-chloro-2-methoxyphenyl)ethanamine (160 mg, 0.862 mmol, 75.1% yield). warming to ambient temperature The reaction was cooled to 0° C. quenched with 174 μL of water, 174 μL of 15% NaOH and 522 μL water After stirring for 1 hour ethyl acetate and MgSO4 was added The reaction mixture was filtered concentrated

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

Procedure: A portion of 2-(2-bromo-4-chlorophenyl)acetonitrile (7.1 g; 39.1 mmol) was directly dissolved in borane solution (78.2 mL of a 1.0 M solution in tetrahydrofuran; 78.2 mmol), and the resulting solution was stirred and heated to reflux. After refluxing for a total of 90 minutes, the heat was removed and the solution was allowed to cool for a few minutes, and then 16 mL of methanol was carefully added to quench the solution. The resulting solution was again heated to reflux for 30 minutes. The solvent was then evaporated, and the residue was partitioned between 200 mL of 1M HCl (aq.) and 200 mL ether. The aqueous layer was filtered to remove a small amount of suspended insoluble material, and the pH of the filtrate was adjusted to pH>12 by the addition of 42% NaOH (aq.). The filtrate was then extracted with 200 mL dichloromethane. The organic layer was dried over sodium sulfate and evaporated to give 3.89 g of 2-(4-chloro-2-methoxyphenyl)ethanamine as a colorless liquid. MS (apci, pos) m/z=186. heated to reflux After refluxing for a total of 90 minutes the heat was removed to cool for a few minutes 16 mL of methanol was carefully added to quench the solution The resulting solution was again heated to reflux for 30 minutes The solvent was then evaporated the residue was partitioned between 200 mL of 1M HCl (aq.) and 200 mL ether The aqueous layer was filtered to remove a small amount of suspended insoluble material the pH of the filtrate was adjusted to pH>12 by the addition of 42% NaOH (aq.) The filtrate was then extracted with 200 mL dichloromethane The organic layer was dried over sodium sulfate evaporated

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (E)-4-chloro-2-methoxy-1-(2-nitrovinyl)benzene (245 mg, 1.15 mmol) was diluted with THF (1 mL), placed under nitrogen and cooled to 0° C. LAH (4588 μL, 4.59 mmol) was added dropwise and the reaction was stirred for 5 hours warming to ambient temperature. The reaction was cooled to 0° C. and quenched with 174 μL of water, 174 μL of 15% NaOH and 522 μL water. After stirring for 1 hour, ethyl acetate and MgSO4 was added. The reaction mixture was filtered and concentrated to yield 2-(4-chloro-2-methoxyphenyl)ethanamine (160 mg, 0.862 mmol, 75.1% yield). warming to ambient temperature The reaction was cooled to 0° C. quenched with 174 μL of water, 174 μL of 15% NaOH and 522 μL water After stirring for 1 hour ethyl acetate and MgSO4 was added The reaction mixture was filtered concentrated

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

Procedure: A portion of 2-(2-bromo-4-chlorophenyl)acetonitrile (7.1 g; 39.1 mmol) was directly dissolved in borane solution (78.2 mL of a 1.0 M solution in tetrahydrofuran; 78.2 mmol), and the resulting solution was stirred and heated to reflux. After refluxing for a total of 90 minutes, the heat was removed and the solution was allowed to cool for a few minutes, and then 16 mL of methanol was carefully added to quench the solution. The resulting solution was again heated to reflux for 30 minutes. The solvent was then evaporated, and the residue was partitioned between 200 mL of 1M HCl (aq.) and 200 mL ether. The aqueous layer was filtered to remove a small amount of suspended insoluble material, and the pH of the filtrate was adjusted to pH>12 by the addition of 42% NaOH (aq.). The filtrate was then extracted with 200 mL dichloromethane. The organic layer was dried over sodium sulfate and evaporated to give 3.89 g of 2-(4-chloro-2-methoxyphenyl)ethanamine as a colorless liquid. MS (apci, pos) m/z=186. heated to reflux After refluxing for a total of 90 minutes the heat was removed to cool for a few minutes 16 mL of methanol was carefully added to quench the solution The resulting solution was again heated to reflux for 30 minutes The solvent was then evaporated the residue was partitioned between 200 mL of 1M HCl (aq.) and 200 mL ether The aqueous layer was filtered to remove a small amount of suspended insoluble material the pH of the filtrate was adjusted to pH>12 by the addition of 42% NaOH (aq.) The filtrate was then extracted with 200 mL dichloromethane The organic layer was dried over sodium sulfate evaporated

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (E)-4-chloro-2-methoxy-1-(2-nitrovinyl)benzene (245 mg, 1.15 mmol) was diluted with THF (1 mL), placed under nitrogen and cooled to 0° C. LAH (4588 μL, 4.59 mmol) was added dropwise and the reaction was stirred for 5 hours warming to ambient temperature. The reaction was cooled to 0° C. and quenched with 174 μL of water, 174 μL of 15% NaOH and 522 μL water. After stirring for 1 hour, ethyl acetate and MgSO4 was added. The reaction mixture was filtered and concentrated to yield 2-(4-chloro-2-methoxyphenyl)ethanamine (160 mg, 0.862 mmol, 75.1% yield). warming to ambient temperature The reaction was cooled to 0° C. quenched with 174 μL of water, 174 μL of 15% NaOH and 522 μL water After stirring for 1 hour ethyl acetate and MgSO4 was added The reaction mixture was filtered concentrated

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

Procedure: A portion of 2-(2-bromo-4-chlorophenyl)acetonitrile (7.1 g; 39.1 mmol) was directly dissolved in borane solution (78.2 mL of a 1.0 M solution in tetrahydrofuran; 78.2 mmol), and the resulting solution was stirred and heated to reflux. After refluxing for a total of 90 minutes, the heat was removed and the solution was allowed to cool for a few minutes, and then 16 mL of methanol was carefully added to quench the solution. The resulting solution was again heated to reflux for 30 minutes. The solvent was then evaporated, and the residue was partitioned between 200 mL of 1M HCl (aq.) and 200 mL ether. The aqueous layer was filtered to remove a small amount of suspended insoluble material, and the pH of the filtrate was adjusted to pH>12 by the addition of 42% NaOH (aq.). The filtrate was then extracted with 200 mL dichloromethane. The organic layer was dried over sodium sulfate and evaporated to give 3.89 g of 2-(4-chloro-2-methoxyphenyl)ethanamine as a colorless liquid. MS (apci, pos) m/z=186. heated to reflux After refluxing for a total of 90 minutes the heat was removed to cool for a few minutes 16 mL of methanol was carefully added to quench the solution The resulting solution was again heated to reflux for 30 minutes The solvent was then evaporated the residue was partitioned between 200 mL of 1M HCl (aq.) and 200 mL ether The aqueous layer was filtered to remove a small amount of suspended insoluble material the pH of the filtrate was adjusted to pH>12 by the addition of 42% NaOH (aq.) The filtrate was then extracted with 200 mL dichloromethane The organic layer was dried over sodium sulfate evaporated