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

HRID 456908ノート

反応式

HRID 456908 の反応式
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

参加物

4

反応物 2

HCID 176Acetic AcidHCID 146166232-Chloro-3-iodoquinoline

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

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. 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 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).

後処理

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

出典と根拠

ORDレコード
ord-218604c5c8fc429d8e6868f73740ddd5
出典データセット
uspto-grants-2007_03
特許番号
US07186723B2

反応ノート

読み込み中…