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

HRID 1375427Notes

Reaction equation

HRID 1375427 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 hours 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. A suspension of the desired product was isolated by vacuum filtration followed by washing with water (50 mL). The water and traces of acetic acid were removed under vacuum for 5 hours to afford 3-iodo-1H-quinolin-2-one (1-3) as a tan powder. 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 hours to completion by TLC analysis of the crude
  2. customreaction mixture
  3. temperatureto cool to ambient temperature

Sources & evidence

ORD record
ord-ebff96605a564bfc96b0d17db6ffa4f4
Source dataset
uspto-grants-2007_01
Patent number
US07169788B2

Reaction notes

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