Nitromethane → HCID 118342895, 화합물

HRID 2202689노트

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HRID 2202689 반응식
[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[CH:12]=[O:13])=[CH:9][CH:8]=[CH:7][CH:6]=2.C(=O)([O-])[O-].[K+].[K+].[N+:20]([CH3:23])([O-:22])=[O:21]>C1COCC1>[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[CH:12]([OH:13])[CH2:23][N+:20]([O-:22])=[O:21])=[CH:9][CH:8]=[CH:7][CH:6]=2

참가 물질

5

반응물 3

HCID 6375NitromethaneHCID 11430Potassium CarbonateHCID 17974702HCID 17974702, 화합물

생성물 1

HCID 118342895HCID 118342895, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a brown clear solution of 3-chloroquinoline-4-carbaldehyde (A275-3) (0.362 g, 1.89 mmol) in THF (1.9 mL) at room temperature was added potassium carbonate (0.078 g, 0.566 mmol) and nitromethane (1.420 mL, 26.4 mmol). The brown homogeneous mixture was stirred at room temperature. After 4 h, the reaction mixture was quenched with water (50 mL) and extracted with EtOAc (2×50 mL). The organic extract washed with saturated NaCl (1×50 mL), and dried over Na2SO4. The solution was filtered, concentrated in vacuo, and dried under high vacuum to give 1-(3-chloroquinolin-4-yl)-2-nitroethanol (A275-4) as a brown solid. 1H NMR (400 MHz, DMSO-d6) δ 8.88-8.93 (1H, m), 8.73 (1H, dd, J=8.6, 0.8 Hz), 8.08 (1H, dd, J=8.4, 1.0 Hz), 7.82 (1H, ddd, J=8.4, 6.9, 1.5 Hz), 7.72 (1H, ddd, J=8.5, 6.9, 1.4 Hz), 6.91 (1H, dd, J=4.5, 1.0 Hz), 6.26 (1H, ddd, J=10.0, 4.6, 3.6 Hz), 5.03-5.12 (1H, m), 4.94-5.01 (1H, m); LC-MS (ESI) m/z 253.1 (M+H)+.

후처리

  1. customthe reaction mixture was quenched with water (50 mL)
  2. extractionextracted with EtOAc (2×50 mL)
  3. extractionThe organic extract
  4. washwashed with saturated NaCl (1×50 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationThe solution was filtered
  7. concentrationconcentrated in vacuo
  8. customdried under high vacuum

출처 및 근거

ORD 기록
ord-9dc0a3fd862f45ffb2e8f20f62fcf2c3
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09365522B2

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