hydrogen fluoride in acetonitrile T=20°C; Hydrolysis; 1 h;

quinoline; hydrogen; Lindlar's catalyst P=760.051 Torr;

1: 96 percent / diisopropyl carbodiimide; DMAP / CH2Cl2 / 3 h / 20 °C 2: 77 percent / CH2Cl2 / Mo[N(t-Bu)(p-PhF)]3/CH2Cl2 / toluene / 16 h / 80 °C 3: 86 percent / H2; quinoline / Lindlar catalyst / hexane / 2 h / 760.05 Torr 4: 88 percent / aq. HF / acetonitrile / 1 h View Scheme

1: 86 percent / H2; quinoline / Lindlar catalyst / hexane / 2 h / 760.05 Torr 2: 88 percent / aq. HF / acetonitrile / 1 h View Scheme

1: 0.2368 g / aq. AcOH / tetrahydrofuran / 9 h / 20 °C 2: 96 percent / diisopropyl carbodiimide; DMAP / CH2Cl2 / 3 h / 20 °C 3: 77 percent / CH2Cl2 / Mo[N(t-Bu)(p-PhF)]3/CH2Cl2 / toluene / 16 h / 80 °C 4: 86 percent / H2; quinoline / Lindlar catalyst / hexane / 2 h / 760.05 Torr 5: 88 percent / aq. HF / acetonitrile / 1 h View Scheme

1: 0.2368 g / aq. AcOH / tetrahydrofuran / 9 h / 20 °C 2: 96 percent / diisopropyl carbodiimide; DMAP / CH2Cl2 / 3 h / 20 °C 3: 77 percent / CH2Cl2 / Mo[N(t-Bu)(p-PhF)]3/CH2Cl2 / toluene / 16 h / 80 °C 4: 86 percent / H2; quinoline / Lindlar catalyst / hexane / 2 h / 760.05 Torr 5: 88 percent / aq. HF / acetonitrile / 1 h View Scheme

1: 0.2368 g / aq. AcOH / tetrahydrofuran / 9 h / 20 °C 2: 96 percent / diisopropyl carbodiimide; DMAP / CH2Cl2 / 3 h / 20 °C 3: 77 percent / CH2Cl2 / Mo[N(t-Bu)(p-PhF)]3/CH2Cl2 / toluene / 16 h / 80 °C 4: 86 percent / H2; quinoline / Lindlar catalyst / hexane / 2 h / 760.05 Torr 5: 88 percent / aq. HF / acetonitrile / 1 h View Scheme

1: 77 percent / CH2Cl2 / Mo[N(t-Bu)(p-PhF)]3/CH2Cl2 / toluene / 16 h / 80 °C 2: 86 percent / H2; quinoline / Lindlar catalyst / hexane / 2 h / 760.05 Torr 3: 88 percent / aq. HF / acetonitrile / 1 h View Scheme

1: imidazole / dimethylformamide / 24 h / 20 °C 3: aq. AcOH / tetrahydrofuran / 3 h / 20 °C 4: 94 percent / diisopropyl carbodiimide; DMAP / CH2Cl2 / 3 h / 20 °C 5: 73 percent / [Mo{N(tBu)(3,5-Me2C6H3}3] / CH2Cl2; toluene / 16 h / 80 °C 6: 86 percent / H2 / Lindlar catalyst; quinoline / hexane / 2 h / 20 °C / 760 Torr 7: 88 percent / aq. HF / acetonitrile / 1 h / 20 °C View Scheme

2: aq. AcOH / tetrahydrofuran / 3 h / 20 °C 3: 94 percent / diisopropyl carbodiimide; DMAP / CH2Cl2 / 3 h / 20 °C 4: 73 percent / [Mo{N(tBu)(3,5-Me2C6H3}3] / CH2Cl2; toluene / 16 h / 80 °C 5: 86 percent / H2 / Lindlar catalyst; quinoline / hexane / 2 h / 20 °C / 760 Torr 6: 88 percent / aq. HF / acetonitrile / 1 h / 20 °C View Scheme