hydrogenchloride; thionyl chloride in 1,4-dioxane; methanol T=25°C; 18 h;

hydrogenchloride; thionyl chloride in 1,4-dioxane; methanol T=-10 - 21°C; Esterification; 18 h; SOCl2 adding to a pre-cooled susp. of the acid in MeOH, stirring under Ar, evapg., treated with aq. K2CO3 and with 4 N HCl;

1: 98 percent / AcOH / 17.5 h / 6 - 21 °C / Et2NH in AcOH and 30 min after aq. CH2O mixing at 6 deg C; pouring into a pre-cooled indole; quenching with 10 percent NaOH 2: 90 percent / tetrahydrofuran; H2O / MeI adding to a pre-cooled indole (5 deg C) in THF; stirring overnight; aq. KCN adding; stirring at reflux under Ar 3: 77 percent / Na / 2.5 h / 90 - 105 °C / Na adding insmall portions to a soln. of the indole in (EtO)2CO at 90 deg C; stirring 2 h at 105 deg C; evapg. 4: 91 percent / H2 / Raney-Ni W-2 / 8 h / 21 °C / 2585.74 Torr / in the excess of Ac2O 5: 88 percent / aq. NaOH / 8 h / refluxing under Ar; diluting with H2O; acidifying with AcOH up to pH 6.12; ppt. collecting by vacuum filtration 6: 77 percent / SOCl2; HCl / methanol; dioxane / 18 h / -10 - 21 °C / SOCl2 adding to a pre-cooled susp. of the acid in MeOH, stirring under Ar, evapg., treated with aq. K2CO3 and with 4 N HCl View Scheme

1: 77 percent / Na / 2.5 h / 90 - 105 °C / Na adding insmall portions to a soln. of the indole in (EtO)2CO at 90 deg C; stirring 2 h at 105 deg C; evapg. 2: 91 percent / H2 / Raney-Ni W-2 / 8 h / 21 °C / 2585.74 Torr / in the excess of Ac2O 3: 88 percent / aq. NaOH / 8 h / refluxing under Ar; diluting with H2O; acidifying with AcOH up to pH 6.12; ppt. collecting by vacuum filtration 4: 77 percent / SOCl2; HCl / methanol; dioxane / 18 h / -10 - 21 °C / SOCl2 adding to a pre-cooled susp. of the acid in MeOH, stirring under Ar, evapg., treated with aq. K2CO3 and with 4 N HCl View Scheme

1: 91 percent / H2 / Raney-Ni W-2 / 8 h / 21 °C / 2585.74 Torr / in the excess of Ac2O 2: 88 percent / aq. NaOH / 8 h / refluxing under Ar; diluting with H2O; acidifying with AcOH up to pH 6.12; ppt. collecting by vacuum filtration 3: 77 percent / SOCl2; HCl / methanol; dioxane / 18 h / -10 - 21 °C / SOCl2 adding to a pre-cooled susp. of the acid in MeOH, stirring under Ar, evapg., treated with aq. K2CO3 and with 4 N HCl View Scheme

1: 90 percent / tetrahydrofuran; H2O / MeI adding to a pre-cooled indole (5 deg C) in THF; stirring overnight; aq. KCN adding; stirring at reflux under Ar 2: 77 percent / Na / 2.5 h / 90 - 105 °C / Na adding insmall portions to a soln. of the indole in (EtO)2CO at 90 deg C; stirring 2 h at 105 deg C; evapg. 3: 91 percent / H2 / Raney-Ni W-2 / 8 h / 21 °C / 2585.74 Torr / in the excess of Ac2O 4: 88 percent / aq. NaOH / 8 h / refluxing under Ar; diluting with H2O; acidifying with AcOH up to pH 6.12; ppt. collecting by vacuum filtration 5: 77 percent / SOCl2; HCl / methanol; dioxane / 18 h / -10 - 21 °C / SOCl2 adding to a pre-cooled susp. of the acid in MeOH, stirring under Ar, evapg., treated with aq. K2CO3 and with 4 N HCl View Scheme

1: 91 percent / H2 / Raney-Ni W-2 / 8 h / 21 °C / 2585.74 Torr / in the excess of Ac2O 2: 88 percent / aq. NaOH / 8 h / refluxing under Ar; diluting with H2O; acidifying with AcOH up to pH 6.12; ppt. collecting by vacuum filtration 3: 77 percent / SOCl2; HCl / methanol; dioxane / 18 h / -10 - 21 °C / SOCl2 adding to a pre-cooled susp. of the acid in MeOH, stirring under Ar, evapg., treated with aq. K2CO3 and with 4 N HCl View Scheme

1: H2 / Raney Ni / 20 h / 4 Torr 2: 58 percent / 11N NaOH / 8 h / Heating 3: 58 percent / 1.) SOCl2, 2.) 4N HCl / methanol; dioxane / 18 h / 25 °C View Scheme

1: 40 percent / 10N HCl / tetrahydrofuran / 0.75 h / 65 - 70 °C 2: H2 / Raney Ni / 20 h / 4 Torr 3: 58 percent / 11N NaOH / 8 h / Heating 4: 58 percent / 1.) SOCl2, 2.) 4N HCl / methanol; dioxane / 18 h / 25 °C View Scheme

1: 88 percent / aq. NaOH / 8 h / refluxing under Ar; diluting with H2O; acidifying with AcOH up to pH 6.12; ppt. collecting by vacuum filtration 2: 77 percent / SOCl2; HCl / methanol; dioxane / 18 h / -10 - 21 °C / SOCl2 adding to a pre-cooled susp. of the acid in MeOH, stirring under Ar, evapg., treated with aq. K2CO3 and with 4 N HCl View Scheme