Hydrochloric Acid → (E)-2-(2-(Quinolin-2-yl)prop-1-enyl)phenol

HRID 1050920

반응식

HRID 1050920 반응식
[OH-].[Na+].O.C([O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1/[CH:14]=[C:15](/[C:17]1[CH:26]=[CH:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=1)\[CH3:16])(=O)C.Cl>C(O)C>[N:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:25]=[CH:26][C:17]=1/[C:15](/[CH3:16])=[CH:14]/[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[OH:7]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 90025673(E)-2-(2-(Quinolin-2-yl)prop-1-enyl)phenyl Acetate

생성물 1

HCID 136259826(E)-2-(2-(Quinolin-2-yl)prop-1-enyl)phenol수율 71%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
100 °C

실험 절차

Aqueous sodium hydroxide (5%, 8.8 g), followed by water (88 mL) were added to a stirred solution of (E)-2-(2-(quinolin-2-yl)prop-1-enyl)phenyl acetate (2.2 g, 7.3 mmol, 1.0 eq.) in ethanol (110 mL). The resulting mixture was heated at 100° C. for 10 min. The mixture was allowed to cool down a little and the pH was adjusted to 7.0 by careful addition of aqueous hydrochloric acid (10%). The mixture was allowed to cool down to r.t. and was then placed in a freezer (−18° C.) over night. The precipitation formed was isolated by filtration yielding the product (1.35 g, 71%) as a tan solid; 1H NMR (400 MHz, DMSO-d6) δ 2.38 (s, 3H, CH3), 6.87 (t, J=7.5 Hz, 1H, Ar), 6.92 (d, J=7.5 Hz, 1H, Ar), 7.16 (t, J=7.5 Hz, 1H, Ar), 7.36 (d, J=7.0 Hz, 1H, Ar), 7.56 (t, J=7.0 Hz, 1H, Ar), 7.61 (s, 1H, C═CH), 7.74 (t, J=7.0 Hz, 1H, Ar), 7.95 (d, J=8.5 Hz, 2H, Ar), 8.00 (d, J=8.5 Hz, 1H, Ar), 8.34 (d, J=8.5 Hz, 1H, Ar), 9.66 (br s, 1H, OH).

후처리

  1. temperatureto cool down a little and the pH
  2. temperatureto cool down to r.t.
  3. waitwas then placed in a freezer (−18° C.) over night
  4. customThe precipitation
  5. customformed
  6. customwas isolated by filtration

출처 및 근거

ORD 기록
ord-c4ae29b680154ff5bd2bde0400fd14c2
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09388138B2

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