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

HRID 431164노트

반응식

HRID 431164 반응식
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

참가 물질

4

반응물 2

HCID 176Acetic AcidHCID 146166232-Chloro-3-iodoquinoline

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
100 °C

실험 절차

The 2-chloro-3-iodoquinoline (1-5, 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 resulting 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 hours to afford the desired quinolinone as a tan powder (1-6). 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).

후처리

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

출처 및 근거

ORD 기록
ord-3a418e8d697f434c9bca705bde9c578f
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06656942B2

반응 노트

불러오는 중…