5-Fluoro-1-indanone → HCID 86762368, 화합물

HRID 2369234노트

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HRID 2369234 반응식
[CH3:1][C:2]1[CH:3]=[C:4]([NH:9]N)[CH:5]=[C:6]([CH3:8])[CH:7]=1.[F:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[C:17](=O)[CH2:16][CH2:15]2>C(O)C.C(O)(=O)C>[F:11][C:12]1[CH:13]=[C:14]2[C:18]([CH2:17][C:16]3[C:3]4[C:2]([CH3:1])=[CH:7][C:6]([CH3:8])=[CH:5][C:4]=4[NH:9][C:15]=32)=[CH:19][CH:20]=1

참가 물질

5

반응물 2

HCID 1365375-Fluoro-1-indanoneHCID 1810602(3,5-dimethylphenyl)hydrazine

생성물 1

HCID 86762368HCID 86762368, 화합물

시약·촉매·용매 2

HCID 176Acetic Acid촉매HCID 702Ethanol용매

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온도
85 °C

실험 절차

To a solution of 3,5-dimethylphenylhydrazine (2.54 g, 14.7 mmol) and 5-fluoro-1-indanone (2.21 g, 14.7 mmol) in ethanol (24 mL) was added glacial acetic acid (3 drops). The solution was stirred at reflux (85° C.) for 15 minutes and cooled to room temperature. Ethanol was removed in vacuo and the resulting orange solid was dissolved in isopropanol (24 mL). Sulfuric acid (36N, 1.65 mL) was added via syringe and the mixture was stirred at reflux (90° C.) for 17 hours and subsequently cooled to room temperature. The solution was basified to pH 10 via addition of aqueous sodium hydroxide (2% by mass) resulting in the formation of a precipitate. The solid was collected by vacuum filtration to yield 47b in 76% crude yield (2.80 g, 11.2 mmol). Crude product was brought on to the next step without further purification. 1H NMR (400 MHz, CDCl3): δ 8.12 (s, 1H), 7.32-7.35 (dd, 1H, J=8.2, 5.2 Hz), 0.24-7.26 (m, 1H), 7.01-7.05 (m, 2H), 6.79 (s, 1H), 3.83 (s, 2H), 2.60 (s, 3H), 2.44 (s, 3H); 13C NMR (150 MHz, CDCl3): δ 160.7 (d, J=361.5), 150.0 (d, J=12.0 Hz), 140.9, 140.6, 131.8, 131.2, 128.9, 122.6, 122.3, 121.6 (d, J=4.5 Hz), 117.2 (d, J=13.5 Hz), 113.4 (d, J=25.5 Hz), 113.1 (d, J=25.5 Hz), 109.6, 31.7 (d, J=3.0 Hz), 21.8, 19.3; 19F NMR (CD3CD, 376 MHz): δ −117.9 (m).

후처리

  1. temperaturecooled to room temperature
  2. customEthanol was removed in vacuo
  3. dissolutionthe resulting orange solid was dissolved in isopropanol (24 mL)
  4. additionSulfuric acid (36N, 1.65 mL) was added via syringe
  5. stirringthe mixture was stirred
  6. temperatureat reflux (90° C.) for 17 hours
  7. temperaturesubsequently cooled to room temperature
  8. additionThe solution was basified to pH 10 via addition of aqueous sodium hydroxide (2% by mass)
  9. customresulting in the formation of a precipitate
  10. filtrationThe solid was collected by vacuum filtration

출처 및 근거

ORD 기록
ord-827dbd6524704bf1b3c6ceef37cc3b13
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08703936B2

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