Hydrochloric Acid → HCID 19699366, 화합물

HRID 70273노트

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HRID 70273 반응식
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[C:7](=O)[CH2:6][CH2:5]2.[N:13](OCCC(C)C)=O.Cl.O>CO>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[CH2:7][CH:6]([NH2:13])[CH2:5]2

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8053Isoamyl NitriteHCID 117689445,6-Difluoro-1-indanone

생성물 1

HCID 19699366HCID 19699366, 화합물

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of 5,6-difluoro-2,3-dihydro-1H-inden-1-one (4.60 g, 27.4 mmol) in MeOH (90 mL) at 40° C. was added isoamyl nitrite (4.17 g, 35.6 mmol) followed by concentrated HCl (2.7 mL). Upon heating for 45 min the solution was cooled to room temperature and water was added. Precipitated solid was collected by filtration and rinsed thoroughly with water affording 3.97 g of a light orange solid. The solid was dissolved in HOAc (100 mL), conc HCl (8 mL) was added, followed by 10% Pd/C (1.07 g). The mixture was hydrogenated under 50 psi H2 for 24 hr using a Parr hydrogenation apparatus, and filtered through a bed of Celite (CHCl3 wash). The filtrate was concentrated in vacuo and the residue was dissolved in water. The aqueous solution was basified with solid K2CO3, extracted with CHCl3 (3×), combined extracts were dried over MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography (MeOH/CH2Cl2) affording the title compound as a brown oil. 1H NMR (400 MHz, CDCl3) δ 6.95 (t, 2H, J=8.9 Hz), 3.83 (m, 1H), 3.10 (dd, 2H, J=15.8 & 6.8 Hz), 2.60 (dd, 2H, J=15.8 & 5.0 Hz); (M+H) 170, 0.68 min (LC/MS method A).

후처리

  1. temperatureUpon heating for 45 min the solution
  2. customPrecipitated solid
  3. filtrationwas collected by filtration
  4. washrinsed thoroughly with water affording 3.97 g of a light orange solid
  5. dissolutionThe solid was dissolved in HOAc (100 mL)
  6. additionconc HCl (8 mL) was added
  7. filtrationfiltered through a bed of Celite (CHCl3 wash)
  8. concentrationThe filtrate was concentrated in vacuo
  9. dissolutionthe residue was dissolved in water
  10. extractionextracted with CHCl3 (3×)
  11. dry with materialwere dried over MgSO4
  12. concentrationconcentrated in vacuo
  13. customThe residue was purified by flash chromatography (MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-f86a0c96acc64c25834c84d95a188d5b
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822518B2

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