Sodium Carbonate → 4,4-Dimethyl-7-nitro-1,2,3,4-tetrahydroquinoline

HRID 401375Notes

Reaction equation

HRID 401375 reaction equation
[CH3:1][C:2]1([CH3:12])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][CH2:4][CH2:3]1.[N+:13]([O-])([O-:15])=[O:14].[K+].C([O-])([O-])=O.[Na+].[Na+]>OS(O)(=O)=O>[CH3:1][C:2]1([CH3:12])[C:11]2[C:6](=[CH:7][C:8]([N+:13]([O-:15])=[O:14])=[CH:9][CH:10]=2)[NH:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24434Potassium NitrateHCID 132194414,4-Dimethyl-1,2,3,4-tetrahydroquinoline

Product 1

HCID 219614774,4-Dimethyl-7-nitro-1,2,3,4-tetrahydroquinolineYield 50.9%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a mixture of 4,4-dimethyl-1,2,3,4-tetrahydro-quinoline (33 g, 0.2 mol) in H2SO4 (120 mL) was slowly added KNO3 (20.7 g, 0.2 mol) at 0° C. After addition, the mixture was stirred at room temperature for 2 h, carefully poured into ice water and basified with Na2CO3 to pH 8. The mixture was extracted with ethyl acetate (3×200 mL). The combined extracts were washed with water and brine, dried over Na2SO4 and concentrated to give 4,4-dimethyl-7-nitro-1,2,3,4-tetrahydro-quinoline (21 g, 50%).

Workup

  1. customat 0° C
  2. additionAfter addition
  3. extractionThe mixture was extracted with ethyl acetate (3×200 mL)
  4. washThe combined extracts were washed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2973b8ddbfa2435e89e4274e4ff3aee3
Source dataset
uspto-grants-2014_06
Patent number
US08741925B2

Reaction notes

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