Ethyl Acetate → 1,2,3,4-Tetrahydro-1-nitrosoquinoline

HRID 1793502Notes

Reaction equation

HRID 1793502 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[N:11]([O-])=[O:12].[Na+].CCOC(C)=O>CC(O)=O.O>[N:11]([N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1)=[O:12]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 694601,2,3,4-TetrahydroquinolineHCID 23668193Sodium Nitrite

Product 1

HCID 8175751,2,3,4-Tetrahydro-1-nitrosoquinolineYield 96.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

1,2,3,4-Tetrahydroquinoline (2.12 g, 15.9 mmol) was dissolved in AcOH (30 mL) and water (10 mL). The solution was cooled to 0° C. An aqueous solution of NaNO2 (1.20 g, 17.5 mmol in 3 mL water) was added dropwise. The reaction was warmed to RT and stirred 2 hrs. Water (20 mL) and EtOAc (20 mL) were added. The layers were separated and the aqueous phase was extracted (2×20 mL) with EtOAc. The combined organic layers were washed with brine, dried, and concentrated to afford a crude orange oil (2.62 g). The product was purified by column chromatography (20–40% EtOAc/hexane) to afford 1-nitroso-1,2,3,4-tetrahydroquinoline (2.48 g, 96%) as a yellow oil. 1H NMR (CDCl3, 300 MHz) δ 8.07 (d, 1H, J=8.1 Hz), 7.21–7.34 (m, 3H), 3.91 (t, 2H, J=6.2 Hz), 3.81 (t, 2H, J=6.2 Hz), 1.97–2.05 (m, 2H) ppm.

Workup

  1. temperatureThe reaction was warmed to RT
  2. customThe layers were separated
  3. extractionthe aqueous phase was extracted (2×20 mL) with EtOAc
  4. washThe combined organic layers were washed with brine
  5. customdried
  6. concentrationconcentrated
  7. customto afford a crude orange oil (2.62 g)
  8. customThe product was purified by column chromatography (20–40% EtOAc/hexane)

Sources & evidence

ORD record
ord-ec8b60df59774f4f9d28c88a2a48cdfb
Source dataset
uspto-grants-2006_07
Patent number
US07081455B2

Reaction notes

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