2-methylnaphthalen-1-amine

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

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

Procedure: 13.0 g (82.7 mmol) of 1-amino-2-methylnaphthalene in 100 ml of chlorobenzene were mixed with 14.7 g (82.7 mmol) of bis(2-chloroethyl)amine×HCl and refluxed under nitrogen for 90 h. The mixture was then concentrated and partitioned between methylene chloride and water at pH=9, and the organic phase was dried and then concentrated. The crude product was purified by column chromatography (silica gel, mobile phase/THF/methanol/ammonia 85/13/2. 11.6 g (62%) of product were isolated. refluxed under nitrogen for 90 h The mixture was then concentrated partitioned between methylene chloride and water at pH=9 the organic phase was dried concentrated The crude product was purified by column chromatography (silica gel, mobile phase/THF/methanol/ammonia 85/13/2

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

Procedure: 14.7 g (82.7 mM) of bis(2-chloroethyl)amine×HCl were added to 13.0 g (82.7 mM) of 1-amino-2-methylnaphthalene in 100 ml of chlorobenzene and refluxed under nitrogen for 90 h. The mixture was then concentrated and partitioned between methylene chloride and water at pH=9, and the organic phase was dried and concentrated. The crude product was purified by column chromatography (silica gel, mobile phase/THF/methanol/ammonia 85/13/2. 11.6 g (62%) of product were isolated. refluxed under nitrogen for 90 h The mixture was then concentrated partitioned between methylene chloride and water at pH=9 the organic phase was dried concentrated The crude product was purified by column chromatography (silica gel, mobile phase/THF/methanol/ammonia 85/13/2

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

Procedure: 14.7 g (82.7 mM) of bis(2-chloroethyl)amine×HCl were added to 13.0 g (82.7 mM) of 1-amino-2-methylnaphthalene in 100 ml of chlorobenzene and refluxed under nitrogen for 90 h. The mixture was then concentrated and partitioned between methylene chloride and water at pH=9, and the organic phase was dried and concentrated. The crude product was purified by column chromatography (silica gel, mobile phase/THF/methanol/ammonia 85/13/2. 11.6 g (62%) of product were isolated. refluxed under nitrogen for 90 h The mixture was then concentrated partitioned between methylene chloride and water at pH=9 the organic phase was dried concentrated The crude product was purified by column chromatography (silica gel, mobile phase/THF/methanol/ammonia 85/13/2

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

Procedure: A 200-ml round-bottom flask equipped with a heating mantle and connected to a water aspirator vacuum system was charged with 15.0 g (0.1 mcl) 1-amino-2-methylnaphthalene, 16.4 g (0.1 mol) alpha-bromo-gamma-butyrolactone and 10.7 g (0.1 mol) 2,6-dimethylpyridine. The reaction mixture was maintained at about 94°-101° C. and 160 mm of Hg for about 7 hours. The reaction mixture was cooled, diluted with 100 ml acetone and filtered. The filtrate was evaporated under reduced pressure to give an oily residue which was eluted through a silica gel column with 15% acetone/85% petroleum ether to give 14.6 g of 3-(N-2-methylnaphth-1-ylamino)-gamma-butyrolactone, m.p. 92°-94° C. Elemental analysis for C15H15NO2 showed: %C, calc. 75.0, found 74.5; %H, calc. 5.9, found 5.6; %N, calc. 5.8, found 5.6. A 200-ml round-bottom flask equipped with a heating mantle The reaction mixture was maintained at about 94°-101° C. The reaction mixture was cooled filtered The filtrate was evaporated under reduced pressure to give an oily residue which was eluted through a silica gel column with 15% acetone/85% petroleum ether

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

Procedure: 14.7 g (82.7 mM) of bis(2-chloroethyl)amine×HCl were added to 13.0 g (82.7 mM) of 1-amino-2-methylnaphthalene in 100 ml of chlorobenzene and refluxed under nitrogen for 90 h. The mixture was then concentrated and partitioned between methylene chloride and water at pH=9, and the organic phase was dried and concentrated. The crude product was purified by column chromatography (silica gel, mobile phase/THF/methanol/ammonia 85/13/2. 11.6 g (62%) of product were isolated. refluxed under nitrogen for 90 h The mixture was then concentrated partitioned between methylene chloride and water at pH=9 the organic phase was dried concentrated The crude product was purified by column chromatography (silica gel, mobile phase/THF/methanol/ammonia 85/13/2

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

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 8-bromo-2-(1-naphthyl)quinoline (3.25 g, 9.7 mmol), 2-methyl-1-naphthalenamine (1.76 g, 11.2 mmol), Pd(dba)2 (0.12 g, 0.2 mmol), L=(N-[2′-(dicyclohexylphosphino)[1,1′-biphenyl]-2-yl]-N,N-dimethylamine (0.15 g, 0.4 mmol), NaOtBu (1.15 g, 12 mmol) and toluene (20 mL) is stirred for 8 h under an argon atmosphere at 100° C. in oil bath. The mixture is then poured into water and extracted with benzene (3×40 mL). The combined organic phases are washed with water and brine and then concentrated. The residue is purified by column chromatography (silica gel 40, hexane/toluene 4:1). Yield 3.1 g (78%). extracted with benzene (3×40 mL) The combined organic phases are washed with water and brine concentrated The residue is purified by column chromatography (silica gel 40, hexane/toluene 4:1)

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

Procedure: 14.7 g (82.7 mmol) of bis(2-chloroethyl)amine×HCl were added to 13.0 g (82.7 mmol) of 1-amino-2-methylnaphthalene in 100 ml of chlorobenzene, and the mixture was boiled under nitrogen and at reflux for 90 h. The mixture was subsequently evaporated and the residue was partitioned between methylene chloride and water at pH=9; the organic phase was then evaporated after having been dried. The crude product was purified by column chromatography (silica gel, eluent THF/methanol/ammonia 85/13/2. 11.6 g (62%) of product were isolated. at reflux for 90 h The mixture was subsequently evaporated the residue was partitioned between methylene chloride and water at pH=9 the organic phase was then evaporated after having been dried The crude product was purified by column chromatography (silica gel, eluent THF/methanol/ammonia 85/13/2

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

Procedure: 14.7 g (82.7 mmol) of bis(2-chloroethyl)amine×HCl were added to 13.0 g (82.7 mmol) of 1-amino-2-methylnaphthalene in 100 ml of chlorobenzene, and the mixture was boiled under nitrogen and at reflux for 90 h. The mixture was then evaporated and the residue was partitioned between methylene chloride and water at pH=9; the organic phase was then evaporated after having been dried. The crude product was purified by column chromatography (silica gel, eluent THF/methanol/ammonia 85/13/2). 11.6 g (62%) of product were isolated. at reflux for 90 h The mixture was then evaporated the residue was partitioned between methylene chloride and water at pH=9 the organic phase was then evaporated after having been dried The crude product was purified by column chromatography (silica gel, eluent THF/methanol/ammonia 85/13/2)

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

Procedure: 14.7 g (82.7 mmol) of bis(2-chloroethyl)amine×HCl were added to 13.0 g (82.7 mmol) of 1-amino-2-methylnaphthalene in 100 ml of chlorobenzene, and the mixture was boiled under nitrogen and at reflux for 90 h. The mixture was then evaporated and the residue was partitioned between methylene chloride and water at pH=9; the organic phase was then evaporated after having been dried. The crude product was purified by column chromatography (silica gel, eluent THF/methanol/ammonia 85/13/2). 11.6 g (62%) of product were isolated. at reflux for 90 h The mixture was then evaporated the residue was partitioned between methylene chloride and water at pH=9 the organic phase was then evaporated after having been dried The crude product was purified by column chromatography (silica gel, eluent THF/methanol/ammonia 85/13/2)

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

Procedure: 14.7 g (82.7 mmol) of bis(2-chloroethyl)amine×HCl were added to 13.0 g (82.7 mmol) of 1-amino-2-methylnaphthalene in 100 ml of chlorobenzene and the mixture was boiled under nitrogen and at reflux for 90 h. The mixture was then evaporated and the residue was partitioned between methylene chloride and water at pH=9, and the organic phase was evaporated after having been dried. The crude product was purified by column chromatography (silica gel, eluent THF/methanol/ammonia, 85/13/2). 11.6 g (62%) of product were isolated. at reflux for 90 h The mixture was then evaporated the residue was partitioned between methylene chloride and water at pH=9 the organic phase was evaporated after having been dried The crude product was purified by column chromatography (silica gel, eluent THF/methanol/ammonia, 85/13/2)