N-hexyl-2-methoxyaniline

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

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

Procedure: According to the general procedure B, 2-Chloroanisole (72 mg, 0.51 mmol) reacted with n-hexylamine (80 μl, 0.60 mmol) using 1 mol % of Pd(OAc)2, 2 mol % of Ph5FcP(t-Bu)2, and sodium tert-butoxide (58 mg, 0.60 mmol) in toluene at 100° C. to give the title compound (102 mg, 97%) as a colorless oil: 1H-NMR (400 MHz, CDCl3): δ 6.93 (t, 1H, J=8.0 Hz, aryl coupling J=0.9 Hz), 6.82 (d, 1H, J=8.0 Hz), 6.66-6.73 (m, 2H), 4.30 (bs, 1H), 3.89 (s, 3H), 3.17 (t, 2H, J=7.2 Hz), 1.71 (m, 2H), 1.51-1.34 (m, 6H), 0.97 (t, 3H, J=6.4 and 6.8 Hz). 13C{1H}-NMR (100 MHz, CDCl3): δ 146.65, 138.39, 121.23, 116.03, 109.71, 109.24, 55.29, 43.63, 31.63, 29.43, 26.88, 22.58, 14.00. GC/MS(EI): m/z 207 (M+). Anal. Calcd for C13H21NO: C, 75.23; H, 10.21; N, 6.76. Found: C,75.41; H, 10.25; N, 6.69. at 100° C.

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

Procedure: Using the general procedure, 2-bromoanisole (125 μL, 1.0 mmol) was coupled with n-hexylamine (198 μL, 1.5 mmol) at 100° C. for 22 h. Purification of the crude product by column chromatography on silica gel using hexane/ethyl acetate (30:1) as eluent afforded the desired product as a colorless liquid (184 mg, 89% yield). Rf=0.4 (hexane/ethyl acetate=20:1). Purification of the crude product by column chromatography on silica gel

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

Procedure: According to the general procedure B, 2-Chloroanisole (72 mg, 0.51 mmol) reacted with n-hexylamine (80 μl, 0.60 mmol) using 1 mol % of Pd(OAc)2, 2 mol % of Ph5FcP(t-Bu)2, and sodium tert-butoxide (58 mg, 0.60 mmol) in toluene at 100° C. to give the title compound (102 mg, 97%) as a colorless oil: 1H-NMR (400 MHz, CDCl3): δ 6.93 (t, 1H, J=8.0 Hz, aryl coupling J=0.9 Hz), 6.82 (d, 1H, J=8.0 Hz), 6.66-6.73 (m, 2H), 4.30 (bs, 1H), 3.89 (s, 3H), 3.17 (t, 2H, J=7.2 Hz), 1.71 (m, 2H), 1.51-1.34 (m, 6H), 0.97 (t, 3H, J=6.4 and 6.8 Hz). 13C{1H}-NMR (100 MHz, CDCl3): δ 146.65, 138.39, 121.23, 116.03, 109.71, 109.24, 55.29, 43.63, 31.63, 29.43, 26.88, 22.58, 14.00. GC/MS(EI): m/z 207 (M+). Anal. Calcd for C13H21NO: C, 75.23; H, 10.21; N, 6.76. Found: C,75.41; H, 10.25; N, 6.69. at 100° C.

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

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

Procedure: Using the general procedure, 2-bromoanisole (125 μL, 1.0 mmol) was coupled with n-hexylamine (198 μL, 1.5 mmol) at 100° C. for 22 h. Purification of the crude product by column chromatography on silica gel using hexane/ethyl acetate (30:1) as eluent afforded the desired product as a colorless liquid (184 mg, 89% yield). Rf=0.4 (hexane/ethyl acetate=20:1). Purification of the crude product by column chromatography on silica gel

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

Procedure: Using the general procedure, 2-bromoanisole (125 μL, 1.0 mmol) was coupled with n-hexylamine (198 μL, 1.5 mmol) at 100° C. for 22 h. Purification of the crude product by column chromatography on silica gel using hexane/ethyl acetate (30:1) as eluent afforded the desired product as a colorless liquid (184 mg, 89% yield). Rf=0.4 (hexane/ethyl acetate=20:1). Purification of the crude product by column chromatography on silica gel

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

Procedure: Using the general procedure, 2-bromoanisole (125 μL, 1.0 mmol) was coupled with n-hexylamine (198 μL, 1.5 mmol) at 100° C. for 22 h. Purification of the crude product by column chromatography on silica gel using hexane/ethyl acetate (30:1) as eluent afforded the desired product as a colorless liquid (184 mg, 89% yield). Rf=0.4 (hexane/ethyl acetate=20:1). Purification of the crude product by column chromatography on silica gel

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

Procedure: Using the general procedure, 2-bromoanisole (125 μL, 1.0 mmol) was coupled with n-hexylamine (198 μL, 1.5 mmol) at 100° C. for 22 h. Purification of the crude product by column chromatography on silica gel using hexane/ethyl acetate (30:1) as eluent afforded the desired product as a colorless liquid (184 mg, 89% yield). Rf=0.4 (hexane/ethyl acetate=20:1). Purification of the crude product by column chromatography on silica gel

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

Procedure: According to the general procedure B, 2-Chloroanisole (72 mg, 0.51 mmol) reacted with n-hexylamine (80 μl, 0.60 mmol) using 1 mol % of Pd(OAc)2, 2 mol % of Ph5FcP(t-Bu)2, and sodium tert-butoxide (58 mg, 0.60 mmol) in toluene at 100° C. to give the title compound (102 mg, 97%) as a colorless oil: 1H-NMR (400 MHz, CDCl3): δ 6.93 (t, 1H, J=8.0 Hz, aryl coupling J=0.9 Hz), 6.82 (d, 1H, J=8.0 Hz), 6.66-6.73 (m, 2H), 4.30 (bs, 1H), 3.89 (s, 3H), 3.17 (t, 2H, J=7.2 Hz), 1.71 (m, 2H), 1.51-1.34 (m, 6H), 0.97 (t, 3H, J=6.4 and 6.8 Hz). 13C{1H}-NMR (100 MHz, CDCl3): δ 146.65, 138.39, 121.23, 116.03, 109.71, 109.24, 55.29, 43.63, 31.63, 29.43, 26.88, 22.58, 14.00. GC/MS(EI): m/z 207 (M+). Anal. Calcd for C13H21NO: C, 75.23; H, 10.21; N, 6.76. Found: C,75.41; H, 10.25; N, 6.69. at 100° C.