2-Oxobutanoic Acid → 6-Fluoro-3-methyl-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid

HRID 245180

반응식

HRID 245180 반응식
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[O:9][CH3:10].[F:11][C:12]([F:22])([F:21])[C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=O.O=[C:24]([CH2:28][CH3:29])[C:25]([OH:27])=[O:26]>C(O)C>[F:1][C:2]1[CH:8]=[C:7]2[C:5](=[CH:4][C:3]=1[O:9][CH3:10])[N:6]=[C:16]([C:15]1[CH:18]=[CH:19][CH:20]=[C:13]([C:12]([F:22])([F:21])[F:11])[CH:14]=1)[C:28]([CH3:29])=[C:24]2[C:25]([OH:27])=[O:26]

참가 물질

5

반응물 3

HCID 582-Oxobutanoic AcidHCID 679903-(Trifluoromethyl)benzaldehydeHCID 27745334-Fluoro-3-methoxyaniline

생성물 1

HCID 673840026-Fluoro-3-methyl-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid수율 53%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A solution of 4-fluoro-3-(methyloxy)aniline (11.29 g, 80 mmol) and 3-(trifluoromethyl)benzaldehyde (13.93 g, 80 mmol) in ethanol (200 mL) was heated to reflux for 1 h. 2-Oxobutanoic acid (8.17 g, 80 mmol) was added portionwise. The reaction mixture was stirred at reflux for additional 3 h and cooled to room temperature overnight. The solid was collected by filtration, washed with ethanol, and dried to afford 6-fluoro-3-methyl-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (16.05 g, 53% yield). 1H NMR (400 MHz, DMSO-d6) δ 7.94-7.98 (m, 2H), 7.88 (d, J=7.78 Hz, 1H), 7.74-7.80 (m, 1H), 7.71 (d, J=8.53 Hz, 1H), 7.54 (d, J=12.05 Hz, 1H), 4.03 (s, 3H), 2.38 (s, 3H); MS (m/z) 380.1 (M+H+).

후처리

  1. temperatureto reflux for 1 h
  2. temperatureat reflux for additional 3 h
  3. filtrationThe solid was collected by filtration
  4. washwashed with ethanol
  5. customdried

출처 및 근거

ORD 기록
ord-b6a41f12208d4519a1e4e98c1f8c8bc7
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658636B2

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