Acetic Anhydride → 6-Nitro-2-acetoxyquinoline

HRID 751093Notes

Reaction equation

HRID 751093 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N+:10]([O-])=[CH:9][CH:8]=[CH:7]2)([O-:3])=[O:2].[CH3:15][C:16]([O:18]C(C)=O)=[O:17]>>[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([O:18][C:16](=[O:17])[CH3:15])[CH:8]=[CH:7]2)([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 836466-Nitroquinoline N-oxide

Product 1

HCID 597542506-Nitro-2-acetoxyquinolineYield 33%

Procedure

A solution of compound 45A (564 mg, 2.96 mmol) in Ac2O (20 mL) was heated to 145° C. for 5 h. After cooling to rt, the reaction was concentrated and the residue purified by silica gel flash chromatography eluting with CH2Cl2 to give the title compound (227 mg, 33%) as a beige solid. LC/MS m/z 233 [M+H]+.

Workup

  1. concentrationthe reaction was concentrated
  2. customthe residue purified by silica gel flash chromatography
  3. washeluting with CH2Cl2

Sources & evidence

ORD record
ord-b5b8daa762344e7092ea47bbc90c66f5
Source dataset
uspto-grants-2008_07
Patent number
US07405234B2

Reaction notes

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