Hydrochloric Acid → 1,2,3,4-Tetrahydro-1-nitrosoquinoline

HRID 1110014Notes

Reaction equation

HRID 1110014 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.Cl.[N:12]([O-])=[O:13].[Na+]>O>[N:12]([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:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 694601,2,3,4-TetrahydroquinolineHCID 23668193Sodium Nitrite

Product 1

HCID 8175751,2,3,4-Tetrahydro-1-nitrosoquinolineYield 82.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

266.4 g of 1,2,3,4-tetrahydroquinoline were added to a mixture of 330 ml of 12 N hydrochloric acid and 800 g of ice. A solution of 165 g of sodium nitrite in 500 ml of water was added slowly to the mixture over the course of 2 hours while the temperature was kept below 5° C. The reaction mixture was then allowed to warm to room temperature in the course of hour and was extracted twice with 500 ml portions of toluene. The organic phase was separated, washed four times with 300 ml portions of water, dried and evaporated. As a residue, 269 g of crude 1,2,3,4-tetrahydro-1-nitrosoquinoline were obtained as a brownish oil.

Workup

  1. customwas kept below 5° C
  2. extractionwas extracted twice with 500 ml portions of toluene
  3. customThe organic phase was separated
  4. washwashed four times with 300 ml portions of water
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-7a7598f6ef3b49cab343d0f5a769b9a8
Source dataset
uspto-grants-1994_06
Patent number
US05324725

Reaction notes

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