8-Iodo-4-oxo-1,4-dihydroquinoline-3-carboxylic acid → 8-Iodo-4(1H)-quinolinone

HRID 1958450노트

반응식

HRID 1958450 반응식
[I:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10][CH:9]=[C:8](C(O)=O)[C:7]2=[O:15]>C1(OC2C=CC=CC=2)C=CC=CC=1>[I:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10][CH:9]=[CH:8][C:7]2=[O:15]

참가 물질

3

반응물 1

HCID 218975788-Iodo-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

생성물 1

HCID 124036908-Iodo-4(1H)-quinolinone수율 32.6%

시약·촉매·용매 1

HCID 7583Diphenyl Ether용매

실험 절차

8-Iodo-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid (15.69 g, 49.8 mmol) was suspended in phenylether (40 mL) and the mixture heated to boiling. After 30 min, reaction was completed by LCMS. The crude was transferred to a bequer and cooled to room temperature. Hexanes (500 mL) were added and the mixture was stirred for 10 min. The solid was retrieved by filtration, thoroughly washed with hexanes and purified by HPLC to afford 8-iodo-1H-quinolin-4-one as a brownish solid (4.4 g, 23%). 1H NMR (DMSO-d6, 400 MHz) δ 6.14 (d, 1H), 7.09 (t, 1H), 7.88 (d, 1H), 8.08 (dd, 1H), 8.16 (dd, 1H). Exact mass calculated for C9H6INO 270.95, found 271.8 (MH+).

후처리

  1. temperaturethe mixture heated to boiling
  2. customreaction
  3. filtrationThe solid was retrieved by filtration
  4. washthoroughly washed with hexanes
  5. custompurified by HPLC

출처 및 근거

ORD 기록
ord-94ff1d1236184aeebe427e59a167ed56
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08410119B2

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