Nitromethane → HCID 118342895、化合物

HRID 2202689ノート

反応式

HRID 2202689 の反応式
[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

参加物

5

反応物 3

HCID 6375NitromethaneHCID 11430Potassium CarbonateHCID 17974702HCID 17974702、化合物

生成物 1

HCID 118342895HCID 118342895、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-9dc0a3fd862f45ffb2e8f20f62fcf2c3
出典データセット
uspto-grants-2016_06
特許番号
US09365522B2

反応ノート

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