ammonium hydroxide in dichloromethane

1: 37 percent / NaH / N,N-dimethyl-acetamide / 120 °C 2: 34 percent / NaH; CuBr / dioxane / Heating 3: 57 percent / aq. LiOH / dimethylsulfoxide / Heating 4: 58 percent / NaH; NaI; 15-crown-15 / dimethylformamide / 20 °C 5: 100 percent / H2 / Pd/C / ethanol / 20 °C 6: 61 percent / K2CO3 / dimethylformamide / 120 °C 7: 96 percent / aq. LiOH / methanol; tetrahydrofuran / Heating 8: (COCl)2 / CH2Cl2 / 0 - 20 °C 9: NH3 / CH2Cl2 / 20 °C View Scheme

1: 34 percent / NaH; CuBr / dioxane / Heating 2: 57 percent / aq. LiOH / dimethylsulfoxide / Heating 3: 58 percent / NaH; NaI; 15-crown-15 / dimethylformamide / 20 °C 4: 100 percent / H2 / Pd/C / ethanol / 20 °C 5: 61 percent / K2CO3 / dimethylformamide / 120 °C 6: 96 percent / aq. LiOH / methanol; tetrahydrofuran / Heating 7: (COCl)2 / CH2Cl2 / 0 - 20 °C 8: NH3 / CH2Cl2 / 20 °C View Scheme

1: 58 percent / NaH; NaI; 15-crown-15 / dimethylformamide / 20 °C 2: 100 percent / H2 / Pd/C / ethanol / 20 °C 3: 61 percent / K2CO3 / dimethylformamide / 120 °C 4: 96 percent / aq. LiOH / methanol; tetrahydrofuran / Heating 5: (COCl)2 / CH2Cl2 / 0 - 20 °C 6: NH3 / CH2Cl2 / 20 °C View Scheme

1: 57 percent / aq. LiOH / dimethylsulfoxide / Heating 2: 58 percent / NaH; NaI; 15-crown-15 / dimethylformamide / 20 °C 3: 100 percent / H2 / Pd/C / ethanol / 20 °C 4: 61 percent / K2CO3 / dimethylformamide / 120 °C 5: 96 percent / aq. LiOH / methanol; tetrahydrofuran / Heating 6: (COCl)2 / CH2Cl2 / 0 - 20 °C 7: NH3 / CH2Cl2 / 20 °C View Scheme

1: (COCl)2 / CH2Cl2 / 0 - 20 °C 2: NH3 / CH2Cl2 / 20 °C View Scheme

1: 100 percent / SOCl2 / CH2Cl2 / 20 °C 2: 61 percent / K2CO3 / dimethylformamide / 120 °C 3: 96 percent / aq. LiOH / methanol; tetrahydrofuran / Heating 4: (COCl)2 / CH2Cl2 / 0 - 20 °C 5: NH3 / CH2Cl2 / 20 °C View Scheme

1: 61 percent / K2CO3 / dimethylformamide / 120 °C 2: 96 percent / aq. LiOH / methanol; tetrahydrofuran / Heating 3: (COCl)2 / CH2Cl2 / 0 - 20 °C 4: NH3 / CH2Cl2 / 20 °C View Scheme

1: 61 percent / K2CO3 / dimethylformamide / 120 °C 2: 96 percent / aq. LiOH / methanol; tetrahydrofuran / Heating 3: (COCl)2 / CH2Cl2 / 0 - 20 °C 4: NH3 / CH2Cl2 / 20 °C View Scheme

1: 96 percent / aq. LiOH / methanol; tetrahydrofuran / Heating 2: (COCl)2 / CH2Cl2 / 0 - 20 °C 3: NH3 / CH2Cl2 / 20 °C View Scheme