Ethanol → 7-Ethoxy-8-nitroquinoline

HRID 280016Notes

Reaction equation

HRID 280016 reaction equation
Cl[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[Na].[CH2:16]([OH:18])[CH3:17]>>[CH2:16]([O:18][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1)[CH3:17]

Participants

4

Reactant 3

HCID 702EthanolHCID 4597147-Chloro-8-nitroquinolineHCID 5360545Sodium

Product 1

HCID 128498157-Ethoxy-8-nitroquinolineYield 87%

Procedure

A mixture of 7-chloro-8-nitroquinoline (3.00 g, 14.4 mmol), sodium (2.65 g) and absolute ethanol (100 mL) was refluxed for 4.5 hr and cooled. The tan precipitate was filtered off, slurried with water and dried to give title compound as tan solid (2.72 g, 87%); mp 161°-164°. Anal. Calcd for C11H10N2O3 : C, 60.55; H, 4.62; N, 12.84. Found: C, 60.34; H, 4.68; N, 12.78.

Workup

  1. temperaturewas refluxed for 4.5 hr
  2. temperaturecooled
  3. filtrationThe tan precipitate was filtered off
  4. customdried

Sources & evidence

ORD record
ord-04ef76506ae34c9ea248b5ba3e0df2d8
Source dataset
uspto-grants-1986_05
Patent number
US04587342

Reaction notes

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