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

HRID 1875480Notes

Reaction equation

HRID 1875480 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.OS(O)(=O)=O.[N:16]([O-])=[O:17].[Na+]>C(Cl)Cl>[N:16]([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:17]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 694601,2,3,4-TetrahydroquinolineHCID 23668193Sodium Nitrite

Product 1

HCID 8175751,2,3,4-Tetrahydro-1-nitrosoquinoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1,2,3,4-tetrahydroquinoline (10.0 g, 75.08 mmol) in 150 mL CH2Cl2 was added 150 mL 1M H2SO4, followed by NaNO2 (5.70 g, 82.59 mmol). The reaction was stirred for 1.5 hours. The reaction mixture was partitioned, the organic layer retained, washed with a saturated solution of NaCl (aqueous), dried over Na2SO4 and concentrated to give the product (13.4 g 100%) as a dark oil. 1H-NMR (300 MHz, CDCl3): δ 8.08 (d, 1H), 7.28 (m, 3H), 3.92 (m, 2H), 2.82 (m, 2H), 2.03 (m, 2H) ppm; MS m/z calculated for C9H10N2O (M+H): 163.09. Found: 163.1 (M+, ESI+).

Workup

  1. customThe reaction mixture was partitioned
  2. washwashed with a saturated solution of NaCl (aqueous)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customto give the product (13.4 g 100%) as a dark oil

Sources & evidence

ORD record
ord-046c14536bad4a39b312b6c90ec2924d
Source dataset
uspto-grants-2012_11
Patent number
US08309059B2

Reaction notes

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