Acetic Acid → 3-iodo-1H-quinolin-2-one

HRID 1007645Notes

Reaction equation

HRID 1007645 reaction equation
Cl[C:2]1[C:11]([I:12])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C(O)(=[O:15])C>O>[I:12][C:11]1[C:2](=[O:15])[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 146166232-Chloro-3-iodoquinoline

Product 1

HCID 114145753-iodo-1H-quinolin-2-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

The 2-chloro-3-iodoquinoline (1-2, 30.0 g) was weighed into a 250 mL flask and suspended in of 50% aqueous acetic acid (125 mL). The mixture was heated to 100° C. and allowed to reflux for 16 h to completion by TLC analysis of the crude reaction mixture. The mixture was allowed to cool to ambient temperature followed by dilution with 200 mL of water. The resulting a suspension of the desired product was isolated by vacuum filtration follows by washing with water (50 mL). The water and traces of acetic acid were removed under vacuum for 5 h to afford the desired quinolinone as a tan powder (5-5); 1H NMR (500 MHz, CDCl3) δ 12.13 (br s, 1H), 8.71 (s, 1H), 7.65 (d, 1H, J=7.5 Hz), 7.54 (m, 1H), 7.31 (d, 1H, J=8.0 Hz), 7.20 (m, 1H).

Workup

  1. temperatureto reflux for 16 h to completion by TLC analysis of the crude
  2. customreaction mixture
  3. temperatureto cool to ambient temperature

Sources & evidence

ORD record
ord-e15385611c134645a8a970030498e47f
Source dataset
uspto-grants-2004_09
Patent number
US06794393B1

Reaction notes

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