Water → 6-Ethoxy-8-nitroquinoline

HRID 428543Notes

Reaction equation

HRID 428543 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.[CH2:15](Br)[CH3:16].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH2:15]([O:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2)[CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 2262598-Nitroquinolin-6-ol

Product 1

HCID 167725846-Ethoxy-8-nitroquinolineYield 85.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6-hydroxy-8-nitro-quinoline (2.5 g, 13.2 mmol), ethylbromide (1.08 mL, 14.5 mmol), and K2CO3 (4 g, 26.4 mmol) in DMF (50 mL) under a nitrogen atmosphere was heated at 40° C. for 5 hours. The cooled reaction mixture was poured into H2O (200 mL) and extracted into EtOAc (2×200 mL). The organic fractions were combined, dried over NaSO4 and concentrated. The resulting beige solid was triturated with 40% EtOAc/hexane to give 2.46 g (85%) of the title compound as beige crystals.

Workup

  1. customThe cooled reaction mixture
  2. extractionextracted into EtOAc (2×200 mL)
  3. dry with materialdried over NaSO4
  4. concentrationconcentrated
  5. customThe resulting beige solid was triturated with 40% EtOAc/hexane

Sources & evidence

ORD record
ord-a840e82f34cd447e9814ef3f89552fd5
Source dataset
uspto-grants-2001_11
Patent number
US06313126B1

Reaction notes

Loading…