1,2,3,4-Tetrahydroquinoline → 1,2,3,4-Tetrahydro-1-nitrosoquinoline

HRID 717771Notes

Reaction equation

HRID 717771 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+]>Cl.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

5

Reactant 2

HCID 694601,2,3,4-TetrahydroquinolineHCID 23668193Sodium Nitrite

Product 1

HCID 8175751,2,3,4-Tetrahydro-1-nitrosoquinolineYield 82.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

1,2,3,4-Tetrahydroquinoline (10 g, 75 mmol) was dissolved in 3N HCl (50 mL) at 0° C. The reaction mixture was stirred for 5 min. at 0° C., then a solution of sodium nitrite (6.22 g, 90 mmol) in water was added at 0° C., and the mixture stirred for 2 h at RT. After completion of reaction, water was added and the mixture extracted with EtOAc (2×200 mL). The combined organic layers were washed with water, dried over sodium sulfate and concentrated under vacuum to obtain 10 g of product.

Workup

  1. stirringthe mixture stirred for 2 h at RT
  2. additionwas added
  3. extractionthe mixture extracted with EtOAc (2×200 mL)
  4. washThe combined organic layers were washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-b945267a89e14846bc492d9accd6799f
Source dataset
uspto-grants-2015_11
Patent number
US09193728B2

Reaction notes

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