tert-Butoxy bis(dimethylamino)methane → HCID 58683726, compound
Reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].C([O:19]C(N(C)C)N(C)C)(C)(C)C>CN(C=O)C>[N+:12]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[CH:1]=[O:19])[N:9]=[CH:8][CH:7]=[CH:6]2)([O-:14])=[O:13]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
7-Methyl-6-nitroquinolin (1.22 g; 6.5 mmol) and tert.butoxy-bis(dimethylamino)methan (5.2 ml; 27.3 mmol) in DMF (13 ml) were heated for 15 min. in an oil bath, which was preheated to 160° C. The reaction mixture was evaporated to dryness, taken up in THF (26 ml). NalO4 (8.3 g; 39 mmol) in water (520 ml) was added at room. temperature within 1.5 h and after stirring for another 1 h the reaction mixture was extracted with EtOAc twice. The combined organic phases were dried over Na2SO4, evaporated and purified via chromatography (SiO2; TBME) to yield the title compound as a yellow foam (920 mg; 70%).