trichlorophosphate in N,N-dimethyl-formamide; toluene 1.) RT, 10 min, 2.) reflux, 30 min;

1: 98 percent / H2 / Pd 2: trimethyl orthoformate 3: 36 percent / 3-chloroperoxybenzoic acid / CHCl3; CH2Cl2; methanol / 0.5 h / Heating 4: 44 percent / POCl3 / toluene; dimethylformamide / 0.67 h / 20 - 100 °C View Scheme

1: 81 percent / POCl3 2: 95 percent / NH3 3: 98 percent / H2 / Pd 4: trimethyl orthoformate 5: 36 percent / 3-chloroperoxybenzoic acid / CHCl3; CH2Cl2; methanol / 0.5 h / Heating 6: 44 percent / POCl3 / toluene; dimethylformamide / 0.67 h / 20 - 100 °C View Scheme

1: 95 percent / NH3 2: 98 percent / H2 / Pd 3: trimethyl orthoformate 4: 36 percent / 3-chloroperoxybenzoic acid / CHCl3; CH2Cl2; methanol / 0.5 h / Heating 5: 44 percent / POCl3 / toluene; dimethylformamide / 0.67 h / 20 - 100 °C View Scheme

1: 49 percent / Ac2O; CH3COOK 2: 81 percent / POCl3 3: 95 percent / NH3 4: 98 percent / H2 / Pd 5: trimethyl orthoformate 6: 36 percent / 3-chloroperoxybenzoic acid / CHCl3; CH2Cl2; methanol / 0.5 h / Heating 7: 44 percent / POCl3 / toluene; dimethylformamide / 0.67 h / 20 - 100 °C View Scheme

1: 89 percent / HCl 2: 49 percent / Ac2O; CH3COOK 3: 81 percent / POCl3 4: 95 percent / NH3 5: 98 percent / H2 / Pd 6: trimethyl orthoformate 7: 36 percent / 3-chloroperoxybenzoic acid / CHCl3; CH2Cl2; methanol / 0.5 h / Heating 8: 44 percent / POCl3 / toluene; dimethylformamide / 0.67 h / 20 - 100 °C View Scheme

1: trimethyl orthoformate 2: 36 percent / 3-chloroperoxybenzoic acid / CHCl3; CH2Cl2; methanol / 0.5 h / Heating 3: 44 percent / POCl3 / toluene; dimethylformamide / 0.67 h / 20 - 100 °C View Scheme

1: formamide With potassium tert-butylate in dimethyl sulfoxide 0.5 h; 2: 4-chloro-1H-imidazo[4,5-c]-quinoline in dimethyl sulfoxide T=105°C; 2 h; 3: With hydrogenchloride in water; dimethyl sulfoxide pH=8; Product distribution / selectivity;

1: formamide With potassium tert-butylate in isobutyramide 0.5 h; 2: 4-chloro-1H-imidazo[4,5-c]-quinoline in isobutyramide T=120°C; 1 h; Product distribution / selectivity;