Sulfuric Acid → 7-Fluoroquinolin-2(1H)-one

HRID 656856Notes

Reaction equation

HRID 656856 reaction equation
OS(O)(=O)=O.[F:6][C:7]1[CH:8]=[C:9]([NH:13][C:14](=[O:21])[CH2:15][CH:16](OC)OC)[CH:10]=[CH:11][CH:12]=1>O>[F:6][C:7]1[CH:8]=[C:9]2[C:10]([CH:16]=[CH:15][C:14](=[O:21])[NH:13]2)=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 1118Sulfuric Acid2×HCID 68809599N-(3-fluorophenyl)-3,3-bis(methyloxy)propanamide

Product 1

HCID 190675757-Fluoroquinolin-2(1H)-oneYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 70% H2SO4 was made up by adding chilled H2SO4 (35 ml) to chilled water (15 ml) ensuring the temp remained between 10-20° C. Finely ground N-(3-fluorophenyl)-3,3-bis(methyloxy)propanamide (6.17 g, 27.2 mmol) was then added cautiously to this solution keeping the vessel in ice. This was stirred for 1 hour and then ice water (70 ml) was added. This was then diluted further with water (230 ml). The mixture was stirred for a further 30 mins. The precipitate was filtered off and dried in a vacuum oven overnight to give the desired product (3.67 g, 83%). This material contained approximately 10% of the isomeric 5-fluoro-2(1H)-quinolinone.

Workup

  1. additionby adding
  2. customremained between 10-20° C
  3. stirringThe mixture was stirred for a further 30 mins
  4. filtrationThe precipitate was filtered off
  5. customdried in a vacuum oven overnight

Sources & evidence

ORD record
ord-72ece55f44554ecb8c5d176a01947790
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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