Sulfuric Acid → 6-Iodoquinolin-2(1H)-one

HRID 1295445Notes

Reaction equation

HRID 1295445 reaction equation
S(=O)(=O)(O)O.C(O[CH:9]=[CH:10][C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([I:20])=[CH:16][CH:15]=1)=[O:12])C>>[I:20][C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:11](=[O:12])[CH:10]=[CH:9]2

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 541035893-ethoxy-N-(4-iodo-phenyl)-acrylamide

Product 1

HCID 138361846-Iodoquinolin-2(1H)-oneYield 75%

Procedure

Sulfuric acid was slowly added to 3-ethoxy-N-(4-iodo-phenyl)-acrylamide (11.3 g, 36 mmol) with stirring. After stirring for 3 hrs, the reaction mixture was slowing poured into ice (˜300 g). The precipitation was collected by filtration, washed with water and dried. Flash chromatography (Merck Silica gel 60, 230–400 mesh, 0%-15% methanol in methylene chloride in 40 min) afforded 6-iodo-1H-quinolin-2-one (7.23 g, 75%) as a black solid. LC-MS m/e 272 (MH+).

Workup

  1. stirringAfter stirring for 3 hrs
  2. customThe precipitation
  3. filtrationwas collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-e45fc67c860c42a4b9dc999d1281b166
Source dataset
uspto-grants-2007_07
Patent number
US07241893B2

Reaction notes

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