Acetic Anhydride → 6-Fluoro-1,2-dihydroquinolin-2-one

HRID 860022Notes

Reaction equation

HRID 860022 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N+:8]([O-])=[CH:7][CH:6]=[CH:5]2.C(OC(=O)C)(=[O:15])C>>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:15])[CH:6]=[CH:5]2

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 198986466-Fluoro-1-oxo-1lambda~5~-quinoline

Product 1

HCID 98340436-Fluoro-1,2-dihydroquinolin-2-one

Procedure

A solution of 6-fluoroquinoline 1-oxide from Step B (5.0 g, 30.65 mmol) in acetic anhydride (30 mL) is heated at 110° C. for 6.5 hours. The reaction is allowed to stand at room temperature overnight. The solid (1.1 g) is collected and recrystallized from anhydrous ethanol (75 mL). The reddish crystals are collected by filtration and dried under high vacuum to give the title compound (0.653 g), m.p. dec. 269–270° C.

Workup

  1. customThe solid (1.1 g) is collected
  2. customrecrystallized from anhydrous ethanol (75 mL)
  3. filtrationThe reddish crystals are collected by filtration
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-426482cb18f346cc95904b856e8a76d2
Source dataset
uspto-grants-2006_12
Patent number
US07153849B2

Reaction notes

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