Nitromethane → HCID 118342895, compound

HRID 2202689Notes

Reaction equation

HRID 2202689 reaction equation
[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

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 11430Potassium CarbonateHCID 17974702HCID 17974702, compound

Product 1

HCID 118342895HCID 118342895, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-9dc0a3fd862f45ffb2e8f20f62fcf2c3
Source dataset
uspto-grants-2016_06
Patent number
US09365522B2

Reaction notes

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