Imidazole → HCID 18433622, compound

HRID 2306250Notes

Reaction equation

HRID 2306250 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[C:9]([N+:12]([O-:14])=[O:13])[CH:8]=[CH:7][CH:6]=2.[Si:15](Cl)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16].N1C=CN=C1.O>CN(C=O)C>[Si:15]([O:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[C:9]([N+:12]([O-:14])=[O:13])[CH:8]=[CH:7][CH:6]=2)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 23262449HCID 23262449, compound

Product 1

HCID 18433622HCID 18433622, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Hydroxy-5-nitroquinoline, as described above in Step D, (2.86 g, 15.04 mmol), tert-butyldimethylsilyl chloride (2.95 g, 19.55 mmol) and imidazole (3.07 g, 45.12 mmol) were dissolved in DMF (20 mL) and stirred for 2 hours. The reaction mixture was poured into H2O and extracted with Et2O (2×). The combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo, to yield the above-titled compound.

Workup

  1. extractionextracted with Et2O (2×)
  2. dry with materialThe combined organic extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-38275820d04c4037b2590a0f84e710de
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

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