Nitric Acid → 7-Nitro-1,2,3,4-tetrahydroquinoline

HRID 1715852Notes

Reaction equation

HRID 1715852 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-])([OH:13])=[O:12].C(=O)([O-])[O-].[Na+].[Na+]>S(=O)(=O)(O)O>[N+:11]([C:8]1[CH:9]=[C:10]2[C:5]([CH2:4][CH2:3][CH2:2][NH:1]2)=[CH:6][CH:7]=1)([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 10340Sodium CarbonateHCID 694601,2,3,4-Tetrahydroquinoline

Product 1

HCID 2525137-Nitro-1,2,3,4-tetrahydroquinoline

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

Concentrated sulfuric acid (30.00 mL) was cooled to −10° C. with an ice/salt bath. To this, 1,2,3,4-tetrahydro-quinoline (10.60 g, 75.60 mmol) and a solution of nitric acid (99.5%, 4.80 g, 75.60 mmol) in sulfuric acid (15.00 mL) were added simultaneously within 1 hour, so that the temperature of the reaction mixture does not exceed 10° C. The mixture was stirred then for 2.5 hours at −5° C., then poured over ice and treated with sodium carbonate (0.10 kg) until pH 8-9 was reached. The solid was filtered, washing with water, then dissolved in dichloromethane. The organic phase was washed with water, dried over magnesium sulphate and evaporated. 7-Nitro-1,2,3,4-tetrahydro-quinoline was obtained as a viscous brown oil, 13.70 g (85%), 84% purity.

Workup

  1. customdoes not exceed 10° C
  2. additionpoured over ice
  3. filtrationThe solid was filtered
  4. washwashing with water
  5. dissolutiondissolved in dichloromethane
  6. washThe organic phase was washed with water
  7. dry with materialdried over magnesium sulphate
  8. customevaporated

Sources & evidence

ORD record
ord-90b4416446614e3d8e564452c7491a4b
Source dataset
uspto-grants-2010_09
Patent number
US07799933B2

Reaction notes

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