Dimethylformamide → N-(3-(tert-Butyldimethylsilyloxy)propyl)-3-nitroquinolin-4-amine

HRID 2090236Notes

Reaction equation

HRID 2090236 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1O)=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-:3])=[O:2].CN(C=O)C.S(Cl)(Cl)=O.[Si:24]([O:31][CH2:32][CH2:33][CH2:34][NH2:35])([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]>C(Cl)Cl.CCN(CC)CC>[Si:24]([O:31][CH2:32][CH2:33][CH2:34][NH:35][C:13]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=[CH:5][C:4]=1[N+:1]([O-:3])=[O:2])([C:27]([CH3:29])([CH3:30])[CH3:28])([CH3:26])[CH3:25]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 11074190(3-Aminopropoxy)(tert-butyl)dimethylsilaneHCID 178526762HCID 178526762, compound

Product 1

HCID 68429388N-(3-(tert-Butyldimethylsilyloxy)propyl)-3-nitroquinolin-4-amineYield 91.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 3-nitro-quinolin-4-ol (5 g) in DCM (70 mL) was added DMF (2.3 mL) then thionyl chloride (2.1 mL) and the reaction mixture was refluxed for 3 h. The solution was cooled to 0° C. and 3-{[tert-butyl(dimethyl)silyl]oxy}propan-1-amine (6 g) was added followed by dropwise addition of Et3N (12 mL). The reaction mixture was stirred at rt for 2 h, then partitioned between DCM and saturated NaHCO3 solution. The organic layer was washed with water, dried, and the solvent evaporated under reduced pressure. The residue was triturated with iso-hexane to leave the subtitle compound (8.7 g).

Workup

  1. custompartitioned between DCM and saturated NaHCO3 solution
  2. washThe organic layer was washed with water
  3. customdried
  4. customthe solvent evaporated under reduced pressure
  5. customThe residue was triturated with iso-hexane

Sources & evidence

ORD record
ord-e9e810d5960d450b93f1a952b57f5c4e
Source dataset
uspto-grants-2013_05
Patent number
US08436178B2

Reaction notes

Loading…