Ethanol → 7-Ethoxy-8-nitroquinoline

HRID 34455Notes

Reaction equation

HRID 34455 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-294a05094d7f44c086668703ef905cda
Source dataset
uspto-grants-1988_08
Patent number
US04761475

Reaction notes

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